The Life & Times of Charlotte Gilmore
by Chaz746
Summary: Charlotte Gilmore has always been an independent girl. One who strives to be different from her perfect twin sister Rory. So she separates herself from everything that reminds her of her sister and moves to Manhattan. Where she can truly be herself. Charlotte Gilmore. (AU Season 4)
1. Promo

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS**

 **The Life & Times of Charlotte Gilmore: Promo**

 **Plot:** Charlotte Gilmore has always been an independent girl. One who strives to be different from her perfect twin sister Rory. So she separates herself from everything that reminds her of her sister and moves to Manhattan. Where she can truly be herself. Charlotte Gilmore. (AU Season 4)

 **Main Characters Cast:**

*Charlotte Marie Gilmore played by Lucy Hale

*Tristan Dugrey played by Chad Michael Murray

*Michelle Lopez played by Aimee Carrero

*Austin Matthews played by Jayson Blair

*Ethan Walker played by Thomas Deker

*Sienna Miller played by Zendaya Coleman

*Ursula Underwood played by Jane Fonda

 **Recurring Characters Cast:**

Lorelai Gilmore played by Lauren Graham

Rory Gilmore played by Alexis Bledel

Luke Danes played by Scott Patterson

Emily Gilmore played by Kelly Bishop

Richard Gilmore played by Edward Herrmann

Sookie St. James played by Melissa McCarthy

Jess Mariano played by Milo Ventimiglia

Christopher Hayden played by David Sutcliffe


	2. Reflections

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS**

The Life & Times of Charlotte Gilmore Chapter 1: Reflections

Charlotte Gilmore looked at the empty room before her. All the memories that were once in this room still lingering around. Charlotte was getting ready to leave for college in New York City. She had got accepted into _Fashion Institute of Technology_ and an internship at Underwood Designs.

The road to get where Charlotte was going wasn't easy and it only got harder from here. Being the child of Christopher Hayden and Lorelai Gilmore was curse. On one hand you had a father who was barely around growing up. While in the other hand you had a mom trying to be your friend rather than a parent. That's what made her different from her twin sister Rory.

To constantly be reminded that your sister is a genius was kinda the theme in her life. Rory had chosen to attend Yale. Emily and Richard Gilmore were proud of Rory and all her success. They always glossed over whatever Charlotte accomplished. To Emily and Richard; Charlotte was a puzzle. Charlotte worked for everything she owned never asking for anything. They never understood how she never could ask them for anything like her mother and sister. To them money and social standing was everything.

Charlotte shook her head and picked up her purse hanging off the door and smiled one last time at her childhood bedroom. She walked down the stairs and saw her mom and sister entering the house.

"Hey Char where are you headed off too?" Lorelai asked her youngest daughter as she entered further into the house.

Charlotte rolled her eyes at the question and turned towards the boxes and suitcases lined up behind the living room couch.

"Did you forget that me and Michelle are leaving today? You know what don't answer that. It was a stupid question." Charlotte stated pickin up a box and carrying it outside.

Rory looked at her sister and could see once again the tension in the room. Ever since Charlotte decided to move out of the house completely her and Lorelai have been very distant towards each other. She just wished her mom could understand Charlotte better. Even Rory felt how distant Charlotte became once she got her acceptance letter.

Rory decided it was time to end the cold war in the house before Charlotte Left. "Mom you and Char need to clear the air before she leaves".

"I don't know how we got to this point Rory. Charlotte's attitude changed the moment she got that letter. One minute we were all excited to see where both of you would go next fall. The next moment you both were falling apart at the seems." Lorelai explained confused.

Charlotte walked back into the house and picked up another box and walked outside once again.

"That's the problem Charlotte has with everyone. She has always fought for her own identity and not be my shadow. People have repeatedly compared her to me and that's not fair to Charlotte. So I'm happy for her to branch out on her own. You raised us to be independent woman who never have to struggle for anything." Rory said while holding Lorelai's hand.

"Thanks Sweets"

"Now go talk to her so we can go to Luke's before she leaves." Rory said walking into her room.

Charlotte walked back into the house and headed towards the kitchen for a drink. When she got in there she saw her mom sitting at the table by herself. So she sighed and sat down across from her.

"I don't want to leave and we have this tension so let's just put it all on the table." Charlotte stated.

"I want to know where did everything fall apart between us?" Lorelai asked.

"Ever since Rory got into Chilton everyone has always doubted me. I know its not intentional but I need space from everyone. The only place I could think of is in New York where know one knows who Rory Gilmore is. Basically a place that I can call my own." Charlotte said not looking at her mother.

"I never knew you felt like that. Why haven't you ever said something to me?"

"Mom I've always learned how to brush it aside but lately it was getting too much and now that it's time for me to leave I want to fix that." Charlotte explained.

"I am glad that you finally told me how you feel. I mean the last time we had a serious conversation was when Tristan left for military school." Lorelai stated watching her daughters face cringe.

Charlotte hadn't thought of Tristan in a long time. Rory had introduced them and things just took off from there until he kissed another girl at a party. From there things spiraled out of control.

"I haven't really thought about him in over a year Mom. The way things ended made me realize that he wasn't ready for a relationship. Don't get me wrong he hurt me but im not gonna let a guy mess with my head."

Lorelai looked at her daughter with a smile. She was happy she didn't get her problems when it came to men. Hopefully Char would get new experiences in New York.

"Come on lets go to Luke's before you and Michelle leave" Lorelai said getting up with a smile hugging her daughter.

Rory walked out of her room with a smile and watched as her mom and sister were good again. "So are we going to Lukes now?"

"Yeah lets go so I can say goodbye to Luke" Charlotte said putting on her jacket, following her mother and sister out the door.

(Time Skip)

The Gilmore girls entered Luke's diner and sat at a table watching the town through the window. Luke came by and saw all three of them and shook his head and walked over to their table.

"What are you having?" He asked grumpily.

Lorelai looked at the diner owner and smirked deviously making Luke nervous. "Can we get three cups of coffee, one cheese omelet, a stack of pancakes with a side of bacon, and scrambled eggs with French toast and sausage".

"You guys are really trying to die young" Luke states walking away with there order.

Charlotte giggled at Luke as he walked away and turned towards her sister. "I'm so happy that me and Michelle are living together. We've always talked about getting an apartment together."

"I'm excited for you especially with your internship. Everything is falling into place for you. Your going to do so well that maybe they might offer you a job." Rory rambles to Charlotte.

Luke returns with their food and the Gilmore girls begin to eat. All three of them were thinking about what was next to come. For Rory, all her life she's always had her sister to have her back now they were gonna be going to different colleges. Lorelai was thinking the same thing as Rory. Her main concern was wondering if Charlotte was gonna be ok by herself.

Ring! Ring! Ring!

Charlotte opened her purse and saw that it was Michelle calling. She picked up and answered.

"Hey Michelle where are you?" asked Charlotte.

"I am just getting in my car so give me half an hour to be at your house. What are you doing right now?"

"Cool and I'm eating at Luke's one last time before we leave".

"Ok I will see you soon." Then Michelle hangs up.

Lorelai and Rory watched as Char put her phone away and got up from the table and headed towards the counter towards Luke. Luke looked up from what he was doing and saw Charlotte in front of him.

"Luke I wanted to thank you for everything you've done for me over the years. Hell you were practically there for me more than my dad. You gave me my first job and taught me to be self sufficient." Charlotte paused with tears slowly coming down her face.

Then she continued "I always hated the way Jess treated you. All you were trying to do was make his life easier and he fought you every step of the way. Can you watch over mom while me and Rory are gone. I worry about her being by herself and what she might get up to."

Luke smiled a genuine smile and nodded. He grabbed Charlotte in a hug and held her tight. Ever since she was a little girl Charlotte was always different Luke noticed. While Rory was studious, Charlotte on the other hand was adventurous. Luke taught her how to cook and play baseball which helped her get on the Stars Hollow softball team.

Charlotte then attempted to take out some money but Luke stopped her. "Its on the house good luck in New York. I'm proud of you and don't forget there are people who still care about you." Luke said walking upstairs to his apartment.

Char walked back to her table and picked up her bag "Come on guys, Michelle will almost be at the house". She walked out of the diner with Rory and Lorelai following behind her rushing to catch up.

(Time Skip)

When they reached the front porch of the house Michelle's car had pulled up into the driveway.

Michelle walked up to her best friend and said "Well I spoke to our landlord the loft is ready for us to move into. So let's gather your stuff and put it into the car so we can hit the road."

Ten minutes later the car was packed with all of Charlotte's things. Charlotte turned towards her Mom and sister. "I'll call you when I get settled and we can talk about things. I love you guys but it is time for me to leave". She ran up to both of them and pulled them into a hug. Then she slowly let go and headed into the car.

Michelle watched her friend enter the car with watery eyes. "You do know you'll see them for holidays right?"

Charlotte laughed at her best friends question. "Just drive Michelle" Charlotte said.

*So the First Chapter is done and the Second Chapter is titled _"Moving Day"_

*For the next couple of Chapters it will mainly focus on Charlotte settling in Manhattan

PLEASE FOLLOW, FAVORITE, REVIEW, GIVE YOUR HONEST OPINION

CHAZ746


	3. Moving Day Part 1

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS**

The Life & Times of Charlotte Gilmore Chapter 2: Moving Day Part 1

After several hours of driving the girls had finally made it to New York City. Both girls watched the Manhattan skyline as they drove into the city. Charlotte saw people going about their everyday lives. She was excited about living here.

"So where exactly is our apartment Michelle?" Charlotte asked her best friend.

"Our apartment is on the Lower East Side in Greenwich Village. It is already furnished so all we have to do is unpack our stuff. Hopefully if we finish early we can go out to eat." Michelle said looking at the road.

Twenty minutes later the car pulled up in front of the apartment building the girls would be staying. "What floor are we on? I am so excited to see what the rooms are like" Char said excitedly.

Michelle got out of the car with Charlotte following her to the entrance of the apartment complex. When they entered the building a man in a suit was waiting for them. "Hello my name is Leroy Jones and I am the building manager. How can I help you this afternoon?" Mr. Jones asked.

"We are the new tenants moving today it should be under Michelle Lopez and Charlotte Gilmore." Michelle explained.

"Let me check the lease to verify, give me just a moment" Mr Jones stated walking to the front desk.

Charlotte looked around the lobby of the building and couldn't believe she was going to live here. It really hit her in this moment everything she ever wanted was falling into place right before her eyes it seemed only yesterday when she got her acceptance letter.

( _Flashback_ )

 _Charlotte had just finished softball practice and she was exhausted. She just wanted to curl up in a ball and go to sleep. Since today was Friday she had to attend dinner at her grandparents. She wasn't even going to Chilton and she had to be forced to sit and eat with people she couldn't stand._

 _As Charlotte approached her house she saw that her mom's jeep wasn't in the driveway. She walked to the porch and opened the front door and saw mail on the floor of the entryway. Charlotte picked everything up and began to see if anything was for her. All she saw was bills until she saw an envelope addressed to her. Charlotte ripped the sealed part of the envelope and read:_

 _Dear Miss Charlotte Gilmore,_

 _Congratulations on behalf of the Admissions Committee, it is my pleasure to inform you that you have been admitted to:_

 _Fashion Business Management_

 _We hope you will view this admission as your first step to joining a vibrant and rewarding community that values your academic achievement. To reserve your place in the class, please be sure to return the enclosed tuition deposit form before the due date, with your payment._

 _Any condition(s) that may have been placed on your acceptance are enclosed. Please read these carefully. Unless otherwise indicated, all conditions must be met before registration at FIT or you may not be permitted to register._

 _I would like to take the opportunity to offer you my personal congratulations on your admission to FIT. I wish you success in your pursuit of higher education._

 _Sincerely,_

 _Director of Admissions & Strategic Recruitment_

 _Charlotte reread the words on the paper just to make sure it wasn't a mistake. When she applied she didn't think they would accept her. Don't get Charlotte wrong she was just as smart as if not more than Rory; she just didn't apply herself to make people happy. Now that she was accepted the only thing left to do is to tell Lorelai. She was hesitant to tell her mom because she didn't know how she would react._

 _Charlotte broke out of her thoughts when she heard a car pull up in front of the house and she saw it was her mom and Rory. She rushed to put the envelope in her book bag when she heard their voices getting closer to the door._

 _Lorelai opened the door and saw her youngest daughter standing in the foyer like deer in headlights. "Hey sweets we gotta get ready soon if we wanna get to dinner" Lorelai said heading upstairs._

 _Rory smiled at her sister as she walked passed her to room. Char sighed while picking up her book bag. She then headed towards her room to get ready for the unfortunate dinner they all had to go._

( _End Flashback_ )

Charlotte soon notices Mr. Jones approaching her and Michelle. "Ok ladies the apartment is ready for you both to move in and it seems someone paid for the apartment for the next year up until the lease needs to be renewed. You guys are on the sixth floor in apartment E. Now if you ladies have any questions or need my assistance please call the front desk.

Michelle nodded and Mr Jones handed them the keys for the apartment. Michelle headed to the elevator with Charlotte following. When they entered the elevator the doors closed with Michelle pressing the button that leads to their new home. They stood in silence until Charlotte asked a question she soon regretted.

"Did your dad pay the entire rent for the year?" Charlotte asked Michelle who looked angry.

"Yup."

"Maybe he is trying to be apart of your life now".

"Well if he picked up the phone every once in a while and actually stuck by his word I wouldn't be so mad. Look I'm sorry if it seems like I'm taking my anger out on you but you of all people should know what I am going through. Your father was never around like mine. Hell I was lucky if he remembered my birthday." Michelle ranted with tears forming in her eyes.

Michelle's father is Rafael Lopez one of the biggest real estate agents on the east coast. He was never around when Michelle was growing up. Michelle's mother Diana worked at The Independence Inn with Lorelai. Rafael was just like Chris only be around your family when things were convenient. That was what cemented their friendship and made them stronger because of it.

Charlotte hated that her friend was going through these emotions right now. They both moved to New York to get away from the their family problems but no matter where they go that cloud of familiar doubt and pain follows. Char pulls Michelle into a hug just as the elevator door opens on the sixth floor.

The girls soon walked down the hallway until they saw a door with the letter E. Michelle opened the door which led into the living room and kitchen. On the right side when you enter the apartment was the first bedroom. Further into the apartment pass the living room was the second bedroom. Each bedroom had a closet and they both connected with the bathroom.

The Floor Plan:

"So what do you think of the place, Char?"

Charlotte turned to her best friend and said " This place is so perfect for us. I definitely want the bedroom close to the living room. The windows give off a great view of the city. On top of that your not a morning person and all the sunlight will make you cranky.

"True, very true" Michelle replied.

Charlotte learned the hard way when her best friend gets woken up with direct sunlight. Let us just say walking around with a black eye isn't pretty at all.

"Lets go get our stuff out of the car so we can start unpacking our stuff. Then afterwards we can go look for something to eat. The last time I was here was when Rory wanted to see Jess after he left." Char said walking towards the door.

(Time Skip)

After several trips to and from the car the girls started unpacking their things. While Michelle was putting away her clothes, Charlotte was in the living room hooking her iPod up to stereo. Soon music began to play throughout the apartment:

 _I_ _gotta habit called Alexander McQueen_  
 _But I never show it off, cause I still got the dreams_  
 _That I had when I was little, every girl wants to be_  
 _A famous actress, model, superstar, queen_

_You know that you're perfect exactly how you are_  
 _You don't need a bank account or a shiny, fast car_  
 _It's better to be an original, free your inner individual_  
 _And show them how we do_

_Girls will be girls_  
 _Make the sidewalk your runway_  
 _Work, work, work it, oh_  
 _Girls will be girls_  
 _Out here, running this world_  
 _Better watch it_  
 _Girls will be girls_  
 _Girls will be girls_  
 _Girls will be girls_  
 _Girls will be girls_

_You know that I would never bow down to a guy_  
 _Til' I find the one that knows how to makes me come alive_  
 _All my ladies better know if he doesn't treat you right_  
 _Don't you let him win you over, shake him off and say goodbye_

 _You know that you're perfect exactly how you are_  
 _You don't need a bank account or a shiny, fast car_  
 _It's better to be an original, free your inner individual_  
 _And show them how we do_

_Girls will be girls_  
 _Make the sidewalk your runway_  
 _Work, work, work it, oh_  
 _Girls will be girls_  
 _Out here, running this world_  
 _Better watch it_  
 _Girls will be girls_  
 _Girls will be girls_  
 _Girls will be girls_  
 _Girls will be girls_

_Let me see your work, work_  
 _Madonna, vogue, glamour_  
 _Snap, snap, you wanna?_  
 _You can see me work it_  
 _Yeah, yeah, we gotta_  
 _You can see me work it_  
 _Shot, shots, I call 'em_  
 _If you feeling yourself, blast it!_  
 _Then work it and show 'em your assets_  
 _I'm reppin' the baddest bitches_  
 _They swiping the matte lipstick_  
 _And all of us taking over_  
 _We naughty and nice_  
 _Louis bags stacking_  
 _Hunnets for that rich girl life_

_Girls will be girls_  
 _Make the sidewalk your runway_  
 _Work, work, work it, oh_  
 _Girls will be girls_  
 _Out here, running this world_  
 _Better watch it_  
 _Girls will be girls_  
 _Make the sidewalk your runway_  
 _Work, work, work it, oh_  
 _(You better work it for me, work it for me!)_  
 _Girls will be girls_  
 _Out here, running this world_  
 _Better watch it_  
 _Girls will be girls_  
 _Girls will be girls, yeah_

As the song finished Charlotte finished putting the dishes in the cabinet another song began to play:

 _Nobody sees, nobody knows_  
 _We are a secret, can't be exposed_  
 _That's how it is, that's how it goes_  
 _Far from the others, close to each other_

_In the daylight, in the daylight_  
 _When the sun is shining_  
 _On the late night, on the late night_  
 _When the moon is blinding_  
 _In the plain sight, pain sight_  
 _Like stars in hiding_  
 _You and I burn on, on_

_Put two and to-gether, forever will never change_  
 _Two and to-gether will never change_  
 _Nobody sees, nobody knows_  
 _We are a secret, can't be exposed_  
 _That's how it is, that's how it goes_  
 _Far from the others, close to each other_  
 _That's when we uncover, cover, cover_  
 _That's when we uncover, cover, cover_

_My asylum, my asylum is in your arms_  
 _When the world gives heavy burdens_  
 _I can bear a thousand times_  
 _On your shoulder, on your shoulder_  
 _I can reach an endless sky_  
 _Feels like paradise_

_Put two and together, forever will never change_  
 _Two and together will never change_  
 _Nobody sees, nobody knows_  
 _We are a secret, can't be exposed_  
 _That's how it is, that's how it goes_  
 _Far from the others, close to each other_  
 _That's when we uncover, cover, cover_  
 _That's when we uncover, cover, cover_

_We could build a universe right here_  
 _All the world could disappear_  
 _Wouldn't notice, wouldn't care_  
 _We can build a universe right here_  
 _The world could disappear_  
 _I just need you near_

_Nobody sees, nobody knows_  
 _We are a secret, can't be exposed_  
 _That's how it is (It is), that's how it goes (It goes)_  
 _Far from the others, close to each other_  
 _That's when we uncover, cover, cover_  
 _That's when we uncover, cover, cover (Ooh yeah)_  
 _That's when we uncover_

Michelle walked out into the kitchen as the last verse finished and watched as her friend turned to her and rush to turn off the music.

"So you ready to go and get something to eat? Or do you need more time to finish unpacking?" Michelle asks.

"No lets go I'm starving and lets either get Chinese food or pizza." Charlotte said picking up her purse.

"Spoken like a true Gilmore girl. We can finish when we come back" Michelle said heading to the door with Charlotte following her.

*The next chapter will be titled "Moving Day Part 2"

*The Songs are as follow:

 _"Girls Will Be Girls" by Sophie Beem_

 _"Uncover" by Zara Larsson_

*An Old Face Finally makes his debut

* **If you can't see the floor plan here is the link** : .

CHAZ746


	4. Moving Day Part 2

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS **

The Life & Times of Charlotte Gilmore Chapter 3: Moving Day Part 2

It was dark out when the girls reached the lobby of the building. They waved to Mr. Jones as they passed by his desk heading outside. Charlotte was starving and she didn't care what they chose to eat.

"So when do you have to register for classes Char?" Michelle asked her friend as they walked down the street.

"Sometime this week but before I can register I have to speak with an advisor. I got a call earlier this week saying its mandatory for all incoming students. Hopefully things go smoothly." Charlotte replied.

Soon the girls saw an Italian restaurant and they headed inside. When they got inside a waiter came by and led them to a table while checking on the other patrons. While waiting for the waiter to return Michelle pulled out her phone and Charlotte began to look around the restaurant. As she was looking around she saw a guy from the back of his head. He was dressed in a suit looking really good if Charlotte would say so herself.

Before she could see the guys face, she was tapped on her arm. Charlotte turned around and saw that the waiter had returned.

"Sorry for the wait this is my first day. My name is Ethan and I'll be your server for tonight. Can I interest you ladies with the dinner special?" Ethan asked handing them menus.

Looking over the menus really quick; "No Thanks but you can bring me the mushroom ravioli with a nice Caesar salad on the side. Also for my drink can I have a peach iced tea" Michelle replied with wink.

Ethan with a blush turned to Charlotte "What about you?" He asked.

"I will have the chicken alfredo with a glass of raspberry lemonade. Thanks." Charlotte said handing him back the menu.

"Ok your food will be ready for you shortly" Ethan said walking away.

As Ethan walked away Charlotte turned around to see if the mystery guy was still there. Sadly the table he was sitting at was empty at the moment. Michelle looked up from her phone to see her friend staring intently over at the other side of the room.

"What are you staring at over there?" Michelle asked curiously.

"Nothing." Charlotte replied too quickly for Michelle.

"Be happy that I'm not Lorelai." Michelle replied with a grin towards her now blushing friend.

It was no secret to anyone who knows Lorelai that she can talk your ears off until you have a nervous breakdown spilling all your darkest secrets to her. On top of that she would be deviously grinning at you with a jumbo cup of coffee.

"Ok you were right."

"About?"

"Ugh! You're really gonna make me say it?"

"Yup, so quit stalling and get to the point."

"Lorelai would be proud of you evil spawn." Charlotte states with smirk.

"Storytime please."

"There was this super hot mysterious guy over at that empty table earlier. He was gonna turn his head towards me until Ethan got my attention. Just now I turned around to see if he was there but he wasn't." Charlotte explains sadly.

While Charlotte was moping Ethan returned with their food and placed it in front of them. He then asked "I don't mean to pry but why is she sad all of a sudden?"

"She was table watching earlier and this guy whose back was to her was about to show his face until you apparently interrupted her." Michelle answered Ethan with a straight face while Charlotte scowled at her friend.

"Really?" Ethan asked confused.

"Pretty much." Charlotte said stabbing her food harshly with the fork and putting it in her mouth.

"Ok..." Ethan says looking at Charlotte like she needs to be in a straight jacket. Then he turns back to Michelle "You guys want anything else?"

"No were good for now. Thanks for everything."

Ethan walked away and then girls finished their food. They talked about things they needed for the apartment and what they were doing tomorrow. As the girls were eating someone bumped into their table spilling Charlotte's lemonade all on her lap. Charlotte quickly grabbed a napkin and started to try to clean up her lap as much as she could.

"I am so sorry let me pay for your meal or something." A familiar voice said.

Charlotte looked up from her lap and saw the one person she thought she would never see again. Although it had been two years he looked good. He gained quite a bit more muscles but he still had those smoldering looks.

"Tristan?" Charlotte gasped.

Tristan looked at Charlotte with surprise then he smirked smugly. That smirk alone was trouble for Charlotte. Michelle on the other hand was looking at them like they were some horrible love story and all she needed was some popcorn.

"Well if it isn't Mary's little lamb. You look good Char." Tristan said staring intently at Charlotte who was staring into his blue eyes.

"Seems like military school didn't get rid of your cocky demeanor."

Michelle laughed making both Tristan and Charlotte turn to her. They were so wrapped up in each other that they forgot Michelle was there.

"Hey Michelle how've you been?"

"Hi Tristan it's good to see you, I've been living. How was military school?" Michelle asked.

"Military school was great for me. It helped me realize I need to figure out who I needed to be. I was angry all the time." He paused then turned to Charlotte and continued "I also want to apologize to you for how I treated you. You didn't deserve me lashing out to you over my father's treatment towards me. Even when I kissed Summer that wasn't right so, I'm sorry Charlotte." Tristan apologized.

For the first time in a long time Charlotte was speechless. Never did she think she would see Tristan Dugrey apologize and not blame it on something else. She was happy that he finally figured things out for himself.

"Tristan you don't have to apologize. Rory explained to me what was going on after you had left Hartford. I forgave you a long time ago, it is water under the bridge" Charlotte said with a smile to her ex-boyfriend.

Tristan smiled and grabbed a chair from another table and sat down with the girls facing Charlotte. "Listen I'm gonna be in town looking for an apartment and I was wondering if you want to go out sometime?" Tristan asks

Before Charlotte could say anything Michelle answered for her "She would love too". She handed him her phone.

"Great I'll give you my number and you call me when you got some free time" Tristan says taking Michelle's phone typing in his number.

"I'll see you soon Charlotte and it was also good to see you as well Michelle" Tristan says walking away with a wave.

After Tristan jad left the restaurant; five minutes later Ethan returns to their table. While he is collecting the plates on the table Charlotte asks him for the check.

"Oh yeah your mystery man paid for your dinner and said don't forget to call him. Might I add that he gave me a $500 tip. You better snatch him up before someone else does." Ethan says laughing at Charlotte's face of awe and blush with Michelle joining him.

"How do you know he is the mystery guy? Charlotte asked.

"I know he is mystery guy because he also paid the bill for the table that you were staring strongly at. Now you guys have a nice day and maybe I might see you guys around" Ethan says walking away from the table shaking his head.

Michelle watched as Ethan walked away before turning to her best friend. "One thing I can say about him is that he knows how to make a girl want more." Charlotte says to Michelle

"You ready to go back to the apartment and finish unpacking." Michelle asks. Charlotte nods and both girls gather their things and leave the restaurant waving to Ethan as they pass him.

(Time Skip)

After the girls had returned from the restaurant they finished unpacking the rest of their things. When they finished Michelle headed for bed while Charlotte sat in the living room going over the first day she met Tristan and the disaster that followed

( _Flashback_ )

 _Charlotte was watching the circus show what was known as Rory's Chilton party in her grandparents home with a glass of punch. The sad part of the party is that it was also her birthday which conveniently Emily Gilmore ignored. That tiny fact made Charlotte happy that for once she was being ignored. She watched as Rory was dragged around by Emily and it was quite funny in Charlotte's opinion._

 _As Charlotte sat in living room in the corner she didn't notice a certain blond hearthrob behind her watching her as she sat quietly. He had never seen her at school before but she looked familiar. He approached her slowly and tapped her shoulder. She turned around startled and looked at him._

 _"Can I help you with something?" Charlotte asked._

 _"Hi my name is Tristan Dugrey and I was wondering what a pretty girl like you was sitting alone by yourself?" He asked._

 _Charlotte glared at him when she heard his name. She remembered the day Rory came home from her first day of Chilton. The guy in front of her called her sister "Mary" because she looked so innocent. Now it was time to have some fun with this meathead._

 _"I am just observing the party. These type of events are not my thing so to speak."_

 _"So what do you normally do for fun?" He asks_

 _"Wouldn't you like to know."_

 _"Surprise me"_

 _"Kiss guys then walk away leaving them wanting more" She says taking a sip of her drink._

 _"Really?" Tristan asks with an eyebrow raised and a smirk on his face._

 _Charlotte turns to stare at the boy who antagonizes her sister and slowly gets close to him and kisses his cheek and walks away turning her head back to him with a grin and she disappears from his line of sight into the party._

 _Tristan gets up and makes his way to where Charlotte was headed. When he finally sees her she is next to Rory laughing. What Tristan doesn't notice is Richard Gilmore notice him staring at his youngest granddaughter._

 _"Young man I believe we met earlier at the door. Your Janlen's grandson right?" Richard asks Tristan._

 _"Yes Sir Rory introduced us." Tristan replies while shaking Richard's hand._

 _"Might I ask what you were staring at earlier?_

 _"The girl next to Rory I spoke earlier but she never told me her name and now I am intrigued with who she is" Tristan answers the elder Gilmore._

 _"Ah that girl would be Charlotte. She is Rory's younger twin sister." Richard explains to the shocked boy._

 _"Ma- I mean Rory never said she had a twin sister."_

 _"Well Charlotte likes to keep to herself and she doesn't go to Chilton with Rory" Richard states walking away._

 _On the other side of the room Charlotte explains to Rory what she did to Tristan. Rory smiles and hugs her sister then they both laugh making everyone around them look at them. Tristan approached the two sisters with a smug smirk on his face._

 _"Hey Mary why don't you introduce me to your sister" he asked deviously._

 _Knowing the jig was up "Tristan this is my twin sister Charlotte" Rory said while wving her hand in her sister's direction. Charlotte on the other hand looked at Tristan with a smirk of her own and pulled him into a kiss._

 _Rory and everyone else were shocked at Charlotte. At that moment Emily Gilmore walked into the room with Lorelai right behind her. They both stopped in the archway watching Charlotte kiss Tristan._

 _"CHARLOTTE MARIE GILMORE! You stop that right this instance" Emily Gilmore bellowed with rage._

 _Charlotte and Tristan jumped away from each other facing Emily Gilmore's wrath._

 _"How dare you act like a common harlot!" Emily said towards her granddaughter with shame._

 _Lorelai and Rory knew that Emily opened up the door to Pandora's box with that statement. When it comes to Charlotte's virtue she believed that you shouldn't have sex until you are married. So for Emily to call her granddaughter a harlot that was gonna be the end of tonight._

 _"Listen here you old hag I've put up with a lot of crap from you but that is it" Charlotte said yelling at Emily in front of guests._

 _"Honey" Lorelai said attempting to stop her daughter_

 _"No Mom, all our lives she has been looking down at you because you ran away from the life that she forces down people's throat. I am done trying to be nice just for Rory and for her to basically call me a whore. I don't want nothing to do with her or her money. I will never forgive her". Charlotte ranted to her mom while glaring at Emily._

 _"Young lady you are quite disrespectful and frankly I blame you Lorelai" Emily said._

 _"What else is new? Your always so quick to blame mom for things that are not within her control. Have you ever thought that maybe you're the common denominator when there is a problem?" Charlotte states grabbing her jacket from the closet heading for the front door._

 _"Where are you going I'm not done talking to you" Emily called after Charlotte._

 _"I can't be around you anymore I'm done with you. Have nice party everyone happy fucking birthday to me" Charlotte states slamming the door behind her leaving everyone speechless._

 _When Charlotte was leaving she saw Tristan leaning against a Porsche waiting for something._

 _"I'm surprised you didn't stay to watch the fireworks go off". Charlotte said walking to stand in front of him._

 _"I think everyone saw that". Tristan said sarcastically with a smirk._

 _Charlotte grinned then began to walk down the driveway until Tristan said "Where are you going?"_

 _"Home"_

 _"In the Dark? By Yourself" He asked._

 _Charlotte then stopped and turned back around to face Tristan "Why do you have a problem with that or something?"_

 _"How about I take you home? That way i can try to get to know you better."_

 _"I'd like that" Charlotte says going up to Tristan and kisses his cheek again "Maybe your not so bad after all Dugrey" Then gets in his car._

 _Tristan smirks at her statement and runs to the other side of the car and gets in. When he gets in the car her puts on his seatbelt and glances at Charlotte quickly to see she had put on seatbelt and was now looking at him expectantly._

 _"Do I have something on my face?"_

 _"Nope"_

 _"Then what is it?" He asked the girl._

 _"I think this has been the best and worst birthday I have ever had."_

 _"Care to elaborate?" Tristan asks as he starts the car_

 _"Just drive me home Tristan." Charlotte tells him the directions to get her to Stars Hollow_

 _When Tristan drives away from the Gilmore mansion; Charlotte turns away from him and touches his stereo and turns on the radio and Avril Lavigne plays:_

 _ **Yeah, yeah**_  
 _ **Yeah-eah, yeah**_  
 _ **Yeah-eah, yeah**_

_**Why do you look so familiar**_  
 _ **I could swear that I have seen your face before**_

_**I think I like that you seem sincere**_  
 _ **I think I like to get to know you a little bit more**_

_**I think there's something more, life's worth living for**_  
 _ **Who knows what could happen.**_  
 _ **Do what you do, just keep on laughing**_  
 _ **One thing's true, there's always a brand new day**_  
 _ **I'm gonna live today like it's my last day**_

_**Yeah, yeah,**_  
 _ **Yeah-eah, yeah,**_  
 _ **Yeah-eah, yeah**_

_**How do you always have an opinion**_  
 _ **And how do you always find the best way to compromise**_  
 _ **We don't need to have a reason**_  
 _ **We don't need anything**_  
 _ **We're just wasting time**_

_**I think there's something more, life's worth living for**_  
 _ **Who knows what could happen.**_  
 _ **Do what you do, just keep on laughing**_  
 _ **One thing's true, there's always a brand new day**_  
 _ **Who knows what could happen.**_  
 _ **Do what you do, just keep on laughing**_  
 _ **One thing's true, there's always a brand new day**_  
 _ **I'm gonna live today like it's my last day**_

_**Find yourself, cause I can't find you**_  
 _ **Be yourself, who are you?**_  
 _ **Find yourself, cause I can't find you**_  
 _ **Be yourself, who are you?**_

_**Who knows what could happen.**_  
 _ **Do what you do, just keep on laughing**_  
 _ **One thing's true, there's always a brand new day**_

_**So you go and make it happen**_  
 _ **Do your best just keep on laughing**_  
 _ **It's all on you, there's always a brand new day**_

_**Who knows what could happen.**_  
 _ **Do what you do, just keep on laughing**_  
 _ **One thing's true, there's always a brand new day**_  
 _ **I'm gonna live today like it's my last day**_

 _Thirty minutes later Tristan's Porsche pulls up in front of the crap shack and he turns off the car. He looks over in to the seat next to him to see Charlotte asleep. He slowly taps her shoulder and she awakens. Charlotte turns her head around and sees that she is in front of her house._

 _"Thanks for bringing me home" Charlotte said._

 _"No problem, but can I ask you something first?"_

 _Charlotte slowly gets out of the car and leans on the passenger window waiting for Tristan to ask his question._

 _"Why did you kiss me back at your Grandparents?"_

 _Charlotte thought about what she was gonna say and then replied "At first I was going to embarrass you but then I thought about it and realized that I don't know you. I only know what Rory told me. So I thought I would give you the benefit of the doubt and give you a chance. On top of that someone noticed me. You noticed me." Charlotte said walking away from Tristan's car._

 _When she reached the porch she looked back and waved to Tristan as she entered the house._

 _Before Tristan drove off he noticed a piece of paper that read:_

 _Thanks for driving me home here's my number 555-3908 call me anytime – Charlotte Gilmore_

 _Tristan smirked when he put the phone number away in his glove compartment driving off not even noticing Charlotte watching him leave from her bedroom window._

 _(End Flashback_ )

After that night Charlotte stopped going to Friday night dinner's for a year. Till this day Charlotte remembers the way she met Tristan Dugrey.

Charlotte turns off the light in her new bedroom and sees the shining lights of New York City as she falls asleep. On the other side of Manhattan a certain Blonde heartthrob was thinking the exact same thoughts of Charlotte.

*The next chapter will be titled: _"Class Is In Session"_

 _*_ The song(s) are as follow:

 _"Who Knows" by Avril Lavigne_

CHAZ746


	5. Class Is In Session

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS **

The Life & Times of Charlotte Gilmore Chapter 4: Class Is In Session

A couple of days had passed since Charlotte had run into Tristan and she had been busy running around getting ready for school. Her meeting with her school advisor is today so she was getting ready in the bathroom.

Ring! Ring!

"Hello" Charlotte answered her phone on speaker.

"Hey sweets I haven't heard from you in a while. I was wondering how you were settling in?" Lorelai asked.

"Everything is ok we finally unpacked everything so now we are just organizing things. I'm actually glad you called. I wanna know how things are going with you and Rory?""

Well I'm fine, the Inn is doing great, your sister is all setup at Yale, and did I mention your dad called."

Charlotte stopped what she was doing and put the phone to her ear " Can you repeat the last part to me slowly".

"Your dad called to see how Rory and you are doing?"

"What did you say about me since he really only called to speak to you?"

"Charlotte that's not fair your father loves you and your sister. He just wants some type of relationship with you guys.

"No Mom I don't want anything to do with him after what he did to us. He always makes promises he can't keep. He broke us completely and there is nothing to fix on my end considering he is just a sperm donor to me." Charlotte exclaims bitterly.

"Look I know things have been difficult between you guys but he is still your father give him a chance. Rory has why cant you-" Charlotte cuts off her mom

"The reason I don't want anything to do with him is because I lost faith in a man who has promised countless times that he wants things to be better. I don't like talking to or about him because it makes me mad that he can't be a real father and now that he has a new kid he gets to have a do over. On top of that he tried to get back with you and then he throws it back in your face. So NO I am not gonna forgive him. That is the difference between me and Rory, she actually wants him in her life I don't." Charlotte explains to her mom with tears rolling down her face.

"Sweety whatever happens between me and you dad that's between me and him. I wish you didn't feel this way but that is something he is gonna have to fix." Lorelai says

"Look Mom can we talk about this later I actually have something I need your expertise on."Charlotte states emotionally wiping her face.

"Is it boy trouble because that is my favorite topic" Lorelai says happily changing the subject.

"I hate how Intune you are with my problems."

"It is a gift my dear now Mommys ears are begging for you to tell me what boy is making you crazy"

Charlotte waits a moment before she says "Tristan"

"Excuse me I think I heard wrong did you just say Tristan? As in Ex-boyfriend Tristan? The one who was sent away Tristan?" Lorelai asked with surprise.

"Yeah, Michelle and I went out to dinner a couple of nights ago and we bumped into him. More like he bumped into me."

"Wow"

"I know"

"So lay it on me what is the problem?"

"That's the thing I don't know how to feel. One moment I am so happy I saw him, the next I am afraid he's gonna disappear again. I don't want to let him in again only for him to break me again. I mean even though he apologized for everything, I'm just hesitant to start things back up. What do you think Mom?" Charlotte asked her mom.

For the first time in a long time Lorelai Gilmore was stumped. She wanted to tell her daughter to stay away from Tristan but she knew that would push her daughter into his arms. She also knew that when it came to relationships Charlotte lived for the moment and didn't over think things like Rory.

"What does your heart tell you? What does your gut tell you? I can't make a decision for you. It's all on you sweety. Only you can decide if you want to give Tristan another chance. Take what I just said and go with that. Now I have to go to work and when you make decision call me." Lorelai explains to Charlotte hanging up.

Charlotte looks down at the phone and sighs. The advice her mom just gave her confused her even more. She honestly didn't know what she wanted. She decided to deal with it later it's her first day of school.

(Time Skip)

After the emotional conversation with her mother; Charlotte hurrily finishes her make up and gets dressed. Heading into the kitchen she sees Michelle sitting at the kitchen table typing something on her laptop. She heads for the fridge and grabs a yogurt and puts in her bag.

Michelle looks up from her laptop "Good luck on your first day of school Chica".

"Thanks; I'll probably be a little late tonight so I'll see u tomorrow if I don't see you when I get back" Charlotte sasy rushing to gather her things heading for the door.

Charlotte rushes down the hallway when she sees a guy heading into the elevator "Hold the door please".

When Charlotte gets to the elevator the guy is holding the door for her and she swiftly enters in. She presses the button for the lobby

"Thanks for holding it for me"

"No problem. I haven't seen you around here before."

"I just moved in a couple of days ago with my best friend."

"Cool, what is your name by the way?

"Charlotte. Who are you if you don't mind me asking?"

"Austin."

Silence enters the elevator as it descends to the lobby

"So where are you off to if you don't mind me asking?"Austin asks.

"I'm actually on my way for my first day of school."

Austin turns to face Charlotte and asks "Hey listen I know we just met and you seem kinda cool so me and my friends are having a party you should totally come y and bring your roommate."

"Ill think about it but give me your number so you can text me when it is"

Charlotte hands him her phone and he puts his number in just as the door opens. He hands her the phone and waves goodbye. She walks out of the elevator and heads outside to catch a cab.

(Time Skip)

After traveling for an hour Charlotte rushed inside the school. She was ten minutes late for her meeting with the advisor. Students were milling about in the hallways when she saw the advisor's office she saw a familiar face behind the assistant's desk. It was Ethan the waiter from the restaurant.

She approached him slowly and tapped his desk and he looked up from what he was doing. When he saw her face you could see some recognition in his eyes. "Hey we met earlier this week, the names Ethan." He said getting up from the desk.

"Yeah I remember you. What are you doing here?"

"Oh I go to school here. I work in various offices on the camps for service credits"

"Cool. Do you know if the advisor is inside the office?"

"Yes she is I think she is waiting for you. Good luck I'll be waiting out here to show you around. If you dont mind?"

"Not at all the campus is kinda intimidating and it would be nice to know at least one face."

Charlotte turns to the office and knocks on the door.

"Whoever you are you can enter" a woman's voice answers.

Charlotte opens the door and sees a woman behind her desk looking at a magazine. She was flipping at the pages irritably like she wanted to burn the magazine. The woman looked up from what he was doing.

"You must be Charlotte Gilmore welcome. My name is Olivia Walker; please have a seat we have much to discuss." Olivia says to Charlotte who sits down.

Olivia pulls out a folder with Charlotte's name out on top of her desk and opens it sifting through. For the next couple of minutes Charlotte sat in complete silence looking around the office until she saw a photo. The photo was of Olivia standing next to Ursula Underwood.

"Whoa you know Ursula Underwood?" Charlotte asked in amazement.

Olivia looked up from Charlotte's folder and looked at the photo that Charlotte noticed.

"Yeah I used to intern for her back when I was your age." Olivia said reminiscing.

"I have a meeting with her next week to begin my internship."

"Good luck Kid; she is no the most easiest person to deal with. If you can work with her you can work with anyone." Olivia said.

"Thanks I think." Charlotte said nervously.

"Now let's talk about your future goals and aspirations. I see you graduated at the top 10 of your class. Well you are active with Softball so that's good."

"My main goal is to learn the ins and out of a business to make things easier for the consumer rather than make it so the producer gets profit are a standard or higher rate." Charlotte stated.

If Olivia was impressed with Charlotte's statement it didn't show on her face. If anything that made Charlotte more nervous.

"Well you seem to know what you want to do. Also you have an internship ready and waiting for you so all I can say is good luck. We will be meeting again sometime in 2 weeks just to see how you are adjusting to the curriculum." Olivia explains while getting up.

"Thank you for taking the time out of your busy day. I know im not the only student your gonna have to explain this two." Charlotte says heading to the door.

"My son will show you around until the freshman orientation. I wish you the best and good luck with Ursula once again." Olivia said with a small smile.

"Your son?"

"His name is Ethan he is sitting at my assistant's desk."

"Oh we've met before, I'll see myself out now" Charlotte says walking out.

Charlotte closed the door behind her and saw Ethan waiting for her. Now that she thought about it she could see the similarities between them.

"So when were you gonna tell me your mom was the advisor?"

Ethan grinned and scratched the back of his neck. "I normally don't let people know my mom works at the school I'm attending."

"Well you can take me to orientation and then a tour around the campus" Charlotte said looping her arm through his walking out the door.

(Time Skip)

After the Orientation; the next couple of hours Ethan showed Charlotte around the campus. They saw the FIT museum, several art galleries, and finally the dorms. They were now having lunch in one of the dining halls.

"So how long have you been going here?" Charlotte asked Ethan while dipping a fry in ketchup.

"This is my sophomore year here and I can't complain."

"what is it like with your mom working in the same place you go to school? If you don't mind me asking."

"It has its ups and downs but what life style doesn't. The one thing I can thank her for is to not be biased and treat me like any other student. But other than that she gives me my space to let me figure things out on my own" Ethan explains taking a sip of his coffee

"Sounds like my mom, except the part where she works at my school. That would be a bit too much."

They both laughed at that and finish their food and head to the lecture hall. Charlotte decided to invite Ethan to Austin's party.

"Hey listen I got invited to this party in my building and your like the only friend I have at this school so I was wondering if you wanna come?" Charlotte asked Ethan who stopped walking

"Who is having it?"

"This guy I met on my way here this morning. I was running late and he held the elevator for me. I think his name was Austin. I will say he is sexy but he seems a little older than us." Charlotte explained while exchanging numbers with Ethan.

As she continued talking they headed into the lecture hall and saw students rushing to get seats.

"Well listen I have my computer class I will probably see you around. I'll get back to you about the party just send me more the time and day and ill get back to you." Ethan said waving as he left.

With Ethan gone Charlotte was looking for a seat. Eventually she found one in the back of the hall. Next to the empty seat was a girl reading _The New York Times._ She was really into whatever she was reading.

"Hey, is this seat taken?" Charlotte asked.

The girl looked up and shook her head and returned to her newspaper. Charlotte sat down and waited for the Professor to start the class. Ten minutes later a man walks in and sets his briefcase down and looks up at the students.

"Welcome all my name is Harrison Fields and this is "Business 101". I want you all to know that the person sitting next to you will be your partner for the rest of the semester. Get ready Ladies and Gentleman because class is in session." Professor Fields explained.

*The next chapter will be up after Thanksgiving and it will be titled "Fashion Faux Pas"

*Jess will make his appearance next chapter

Chaz746


	6. Fashion Faux Pas

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS**

The Life & Times of Charlotte Gilmore Chapter 5: Fashion Faux Pas

After being in class for over two hours Charlotte was happy to be walking out of the room. On her way out she was tapped on her shoulder and she turned around to see Ethan behind her. A smile lit upon her face once seeing him.

"Hey how was your first class?" Ethan asked.

"Excruciatingly long." Charlotte said exhausted with Ethan following her out of the building.

"So where are you headed right now?"

Charlotte paused and thought really hard about what she was gonna say. Since she had moved to the city she hadn't explored that much. All of a sudden she knew where she wanted to go. When Jess left Stars Hollow after the car crash, Rory had skipped school and missed their moms graduation to go see him. Since Charlotte didn't go she wanted to see what the fuss was about.

"I'm gonna go to Washington Square Park. My sister told me about it the last time she was here. Do you think you could show me how to get there? I can call Michelle to meet us there and we can have dinner right after." Charlotte said.

"That sounds like a plan let me call my mom and tell her to have dinner without me." Ethan states pulling out his phone.

Charlotte pulls out her phone and texts Michelle:

 _C- Hey what are you doing right now?_

 _M- Still organizing stuff for work. Why?_

 _C- Well remember Ethan the waiter from the other night. He goes to school with me and his mother is my advisor. He took me on a tour of the entire campus._

 _M- Cool, I was thinking ordering Chinese and then helping you pick out an outfit for your future date with Tristan if your up to it._

Charlotte reread Michelle's last text and it brought up the phone conversation with her mom earlier. She still had not decided on if she was going to call him. Hopefully walking through the park would help her make a decision. She looked at her phone and replied.

 _C- Ok do you mind if I invite Ethan over since he's like the first friend I met in the city. We are gonna walk around Washington Square Park and wanted to know if you wanna come._

 _M- Sure and then we could go and pick up dinner on the way._

 _C- Sounds like a plan see you in 30._

 _M- C U then_

When she read the last text from Michelle, Charlotte put her phone in her bag and looked around for Ethan. He was coming back to her in a rush.

"So you ready to go?" He asked.

"Yeah, which way is the quickest way to Washington Square Park?"

"Train" Ethan answered simply tugging her arm leading them to the train station.

(Time Skip)

After a quick subway ride Charlotte and Ethan began walking through the park. Charlotte saw people playing music on instruments with small crowds surrounding them. It felt good that she was here. They soon saw a benches and sat down waiting for Michelle.

"While we wait for Michelle I wanna know more about you. Like who is Charlotte?" Ethan asked with a grin on his face.

"Well it depends on who you ask?" Charlotte said bitterly.

Ethan face scrunched up in confusion at Charlotte's reply "What do you mean by that?" He asked cautiously.

Charlotte looked at her new friend and sighed. She then began to tell him her life growing up in Stars Hollow, dealing with her rich snobby Grandparents, ghost of a father, being in the shadow of her twin sister, and Tristan. When she finished Ethan looked at her in a new light.

"Wow, how are you not crazy?"

"Coffee" She said.

They both looked up when they heard Michelle talking into her phone

"I faxed the papers yesterday. If you didn't receive them I can't help you ciao" Michelle said hanging up. "I forgot how stupid people get when it comes to technology".

Charlotte and Ethan laughed at the girl as she sat down next to them.

"How was your first day so far Char?" Michelle asked while applying lipgloss.

"I wanna say good but so far it is only the beginning. To be honest I'm excited and I haven't been in a long time." Charlotte replied happily.

"Good for you chica so when are you gonna call Tristan. He looked really good, especially when he kept staring at you." Michelle stated with a smug face with Ethan nodding in agreement.

"Whatever Michelle." Charlotte said blushing while her friends laugh at her.

Michelle and Ethan then started talking about school and work while Charlotte looked at her surroundings. It was still warm out and children were running and having fun. She saw people sitting on other benches and relaxing. While looking over at the benches someone caught her attention.

This person was reading " _Howl",_ and she knew exactly who he was. Who else would wear a leather jacket in eighty degree weather with a lot of gel in his head.

She got up and headed towards the bench with Michelle and Ethan giving her weird looks. She approached from behind and tapped his shoulder. When the person turned around his facial expression changed from annoyed to surprise and lastly fear.

"Hi Jess, last I heard you were in California chasing after your father."

"Charlotte."

"That is my name?"

"What are you doing here in New York?"

"I clearly just asked you the same thing, which you haven't answered."

Jess stood up from the bench he was sitting on and put his book in jacket. Then he began to walk away from Charlotte. Charlotte then grabbed his arm and made him look at her with a glare.

"You can glare at me all you want but I'm not Rory. I never judged you like Rory because I know what it is like to be tossed aside and you build up this wall to keep yourself from being hurt." She stated.

"I broke your sister's heart and you still try to be my friend. Why?" Jess asked confused.

"No matter what that's what friends are for. My mom may not like you and my sister maybe heartbroken but you still got me Jess." Charlotte says hugging her friend.

When they pull away from each other Jess asks her another question. "So what made you come to my neck of the woods?"

"I needed a change of scenery and to get away from the Gilmore influence. Between my mom, Rory, and the grandparents it was time. You of all people knew what I was going through with everyone comparing me to Rory. So what happened with your dad?" Charlotte said.

"I get it, you wanna make a name for yourself without help I can respect that. I realized he never wanted me cause he wasn't ready to be a father and I am ok with that." Jess said.

"Well at least you got the closure you needed" Charlotte added optimistically.

Jess glanced over and saw Michelle and Ethan watching them.

"I think your friends are waiting for you. Don't want to keep them waiting." Jess said tilting his head in their direction.

"You should come by my apartment sometime and hangout. I will even watch Almost Famous on repeat with you" Charlotte offered.

Jess started to walk away but turned back around and said "your number hasn't changed right?". Charlotte shook her head then Jess continued "Then maybe I might take you up on that offer. See you around Gilmore." Jess then continued walking away until he wasn't seen anymore.

Charlotte then went back to her friends and Michelle noticed the withdrawn look on her face. She then decided to ask the one question that was on her mind.

"Are you gonna tell Rory you saw Jess? I mean I know she and him are not together but she at least deserves to know he is ok." Michelle reasons watching her friends face.

"I don't think I am without Jess' permission. He looks so lost right now and I don't want to lose what trust I have with him. Plus I don't want to get involved in their relationship cause that's not my place." Charlotte explained.

"Well on that note lets go get dinner and watch Netflix guys cause today has been exhausting." Ethan cuts in.

"I agree and I would love some kung pao chicken, fried rice and 2 egg rolls" Michelle adds rubbing her stomach earnestly.

"Come on, let's go find this one some Chinese food before she complains." Charlotte says walking away from her friends. Ethan and Michelle rush to catch up with her and the trio leave the park not noticing Jess watch them leave.

(Time Skip)

After leaving the park the trio picked up some Chinese food and were now sitting in the girls apartment. They had put on Netflix and were watching the _Wedding Crashers_ until Charlottes phone began to ring.

"Sorry guys I'll take this into my room. Continue watching the movie without me." Charlotte said walking out of the living room into her bedroom.

When her bedroom closes she picks up the phone ending the ringing.

"Hello"

"Hi is this Charlotte Gilmore?"

"Yes, this is she."

"Good, I'm calling from Underwood Designs to let you know you need to come in tomorrow. You and the other intern will be meeting with Ursula in her office at eight in the morning. You will see me at the receptions desk when you enter the building. My name is Rafael and I am one of the event coordinators here.

"Ok thank you Rafael for giving me all the info. Is there anything else I should know?" Charlotte asked curiously.

"Well this time of the year we are very busy due to New York Fashion Week coming up so make sure your well rested. So we will see you tomorrow." Rafael hangs up.

Charlotte looks at the city skyline and thinks about her future. Things were looking up for her but she couldn't stop thinking about Jess. When you got to know him

Seeing Jess after four months put things into perspective. He looks so lost right now and Charlotte could see it. When he first came to Stars Hollow Jess was standoffish. Slowly he let people in and that was what scared him. With Luke, Jess finally had a parent and someone he could depend on. Before he fell for Rory they connected on literature and that was the foundation of their relationship. The only person making life hard for Jess was Jess.

Charlotte went back out to the living room and sat down between her friends on the couch. They both turned to her expectantly waiting for something

"What?" Charlotte asks.

"Who just called you? Michelle asks when Ethan gets up to go to the kitchen.

"Underwood Designs" she replied.

"My mom used to work with Ursula Underwood she is not an easy person to deal with." Ethan adds from the kitchen.

"Well I've dealt with Emily Gilmore so I'm prepared to deal with Ursula. I have to be there early too and your mom told me that earlier today during our meeting." Charlotte said eating popcorn.

"Well I hope you impress the old bat and hopefully get free clothes or something" Michelle said.

"I'm gonna need your help picking out an outfit for tomorrow and I want to make a good impression. While we're at it you can also let me borrow that emerald blouse you have. I'm gonna call Tristan and set up a lunch." Charlotte told her roommate who started jumping excitedly.

"This is so great" Michelle paused and stopped jumping before she added "Are you ready to sit down with him one on one? Without anyone to buffer between you guys."

"I know I haven't seen him in two years but I need answers one way or another."

"As long as you know I'm here if you ever need a sounding board." Michelle tells her friend.

Ethan joins the girls back in the living room with a tray of more snacks.

"You guys have more snacks than anyone I know. " Ethan states while chewing on a snickers bar.

The girls look at him and laugh while trying not to knock over the snacks.

"On that note let's go pick out your clothes now while we are still awake." Michelle said heading for Charlotte's bedroom.

"Wait for us" Charlotte yells to her roommate while dragging her other friend.

When Charlotte and Ethan enter her bedroom they see Michelle come out of the closet with several different blouses and slacks. Then she rushes back into the closet and pulls out jeans and sweaters. She places all the clothes on Charlotte's bed and turns to the two of them.

"Try on different clothes until we find the outfit for work and whatever you're going to wear to lunch with Tristan." Michelle tells Charlotte before turning to Ethan "And you take notes from the professionals" she finishes with a cheeky grin.

Ethan and Michelle then sit on the bed waiting for Charlotte to pick something. When she finally does she enters the bathroom with a sigh at the torture she is about to go through. If her mom was here she would have had both outfits ready in twenty minutes.

After trying several clothes for two hours Charlotte had both outfits ready. She was exhausted especially with Michelle saying no to practically everything and Ethan just staring at Michelle like she needed help. Michelle had went to bed already cause she had a meeting in the morning. Right now she was walking Ethan to her door so he could go home.

"Thanks for inviting me over tonight. You and Michelle are pretty cool and hopefully we can do this again." Ethan says to Charlotte.

"I had a good time as well and thanks for today. For showing me around school and being a friend." Charlotte hugs him and then kisses him on the cheek. "Get home safe Ethan and call me when you get there"

"Sure, well goodnight" He walks out of their apartment and Charlotte closes the door behind him. She then begins to clean up the living room after all three of them. Charlotte realized she hadn't had a movie night since before her mom and Rory left for Europe. Just thinking about her mom made her think next weekend she might go see her mom.

When the living room is cleared Charlotte turns off all the lights in the apartment and climbs into her bed and falls asleep instantly.

(The Next Morning)

Michelle is in the kitchen making breakfast when she hears Charlotte coming out her room dressed for work. Charlotte pours herself a cup of coffee and sits down while Michelle sits across from her.

"You slept well last night?" Michelle asks while eating her breakfast.

Charlotte shrugs and looks at the clock on the wall and sees it is time or her to leave. She heads to her room and picked up her purse and went back out to the dining room .

"I'll call you later to dish about work and I can pick up dinner on my way home" Charlotte said putting her jacket on as she walked to their apartment door.

"Sound like a plan good luck" Michelle hollers as Charlotte closes the door.

Charlotte walks down the hallway and passes by her neighbor Austin's door when suddenly it opened with Austin dressed in workout clothes. He looked too good in those shorts Charlotte thought. He was locking his door when he noticed Charlotte walking by him.

"Hey Charlotte, right?" Austin asked.

"Yeah hi again" she replied awkwardly heading for the elevator with Austin right behind her.

"Seems like you guys were having a good time last night" Austin stated adjusting his tank top making Charlotte nervous. He wa

The elevator door opened when they both got in front of it and they entered. While Charlotte was checking the time on her phone Austin was checking her out. He couldn't stop looking at her and he normally wasn't like this.

"So I was wondering are you and your friend still coming to my party this Friday?" Austin asked.

"Depends on work for me but if I'm free we will try to make it. Have a nice run Austin I got to get to work." Charlotte tells her neighbor as the elevator doors open up into the lobby.

Austin watches as she passes by Mr. Jones and waves to him before walking out of the building. He shakes his head and also walks out of the building running in the opposite direction of Charlotte.

(Time Skip)

Charlotte had just stepped off the train and left the subway. She was preparing herself not to be nervous or to show that she is nervous. She seriously needed a pep talk but it was time to be a big girl. She walked for three blocks until she finally saw the building and headed inside. She saw a man talking to a young woman at the front desk.

"Sorry for interupting but can you tell Rafael that Charlotte Gilmore is here to see him for the internship." She tell the receptionist.

"Sure why don't you take a seat with the other intern and wait a moment." The receptionist points to the waiting area.

Charlotte thanks her and sits down in an empty chair across from the other intern. As Michelle would say the competition. The girl looked well put together in Charlotte's opinion which made her more nervous until the girl spoke to her.

"You nervous too?" The girl asked.

"A little bit, I'm Charlotte by the way" Charlotte said holding out her hand to shake.

"Sienna, I just moved here from LA and I miss it already" Sienna replied shaking Charlotte's hand.

"Have you been waiting long?" Charlotte asked Sienna

"No, I got here a couple of minutes before you" Sienna replied.

Soon the girls heard a pair footsteps approaching them and they saw a man stop in front of them. He had an air around him that was just pure confidence and it made both girls hesitant to what was come.

"Ladies I hope you weren't waiting long. I'm Rafael, please follow me upstairs so you can meet Ursula before I give you guys your jobs for the day." Rafael said leading them to the stairs.

As they followed him upstairs they saw the operations of Underwood Designs. People rushing pass them with portfolios, designers pitching ideas to others. Overall it was busy and the girls were excited.

Soon they stopped in front of an office door with the name "Ursula Underwood" and Rafael turned to the girls.

"Now I will see you both after she is done speaking with you." Rafael explained before knocking on Ursula's office door.

"Enter" Ursula voice said behind the door.

Rafael opened the door "Ursula these are the new interns Charlotte Gilmore and Sienna Miller. You wanted to see them before they started working, remember."

Ursula Underwood was dressed to the nines in her one of a kind business suit. She had this eagle eye thing going on as she looked at her new interns. It was unnerving to say the least but she didn't care.

"You can leave us Rafael" Ursula said dismissing Rafael.

Rafael nodded to his boss as he left and walked out of the room leaving the girls with Ursula.

"Let's get down to business shall we. Please take a seat as this shouldn't take to long and I have a lot of things to get done." Ursula said sitting on her desk then continues. "I want you girls to understand something so let me level with you. What you do represents me so I want it known that I expect the best because it is my name that goes out there not yours".

Both girls replied "Yes, Ms. Underwood."

"Also for the love of god please come better dressed next time. You guys look like you walked out of juicy fruit commercial and the colors are bothering my eyes. I don't need walking Fashion Faux Pas' representing me. Now get to work girls and make me proud we can't all sit and look pretty. Even though I do it flawlessly if I say so myself". She says dismissing them the way she did Rafael.

They exit the office and see Rafael waiting for them and he seem relieved when he sees them.

"At least you girls caught her on a good day. She normally asks questions and makes them leave her office in tears. Now that the pleasantries are over lets get you guys settled into your workstations and then you guys will shadow Yolanda at one of our fashion shows we are styling." Rafael explained walking down the hallway with Charlotte and Sienna trailing right behind him to an office with two empty desks.

"This will be where you will be working so get yourselves settled and we will begin." Rafael said leaving the girls to stare at the room in awe.

* **Well first and foremost I saw the** _ **Gilmore Girls: A Year in Life**_ **and it made me angry. Like I hope there is a season 2 because it left things unanswered and that just can't do. I give this a 7 out of 10. Mostly I was pissed with how selfish Rory became and the way she valued herself when it came to Logan. I honestly hope that she finally gets with Jess and finds her happy medium.**

*The next chapter is titled "Lunch With Dugrey" and it will be ready hopefully before the new year.

*The next chapter will deal with the beginnings of Charlotte's internship, finally sitting down with Tristan and getting answers, and Austin's Party.

Chaz746


	7. Lunch With Dugrey

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS**

The Life & Times of Charlotte Gilmore Chapter 6: Lunch With Dugrey

Fifteen minutes later Rafael returned with a short woman following him into the room. They both were carrying tons of Manila envelopes with papers sticking out of them.

"Ladies I would like for you to meet Yolanda Robbins. You guys will be working with her today on the invitations for the Underwood Gala Event that starts off the fall fashion week here in New York City. Each year it is a different event such as a fashion show or an auction. This year Ursula wants it to be showcase for up incoming designers." Rafael explained putting the envelopes on Sienna's desk.

"Before you girls ask yes you will be able to attend and you can bring 1 or 2 people with you." Yolanda added putting her envelopes on Charlotte's desk.

"How many people will be attending the event?" Sienna asked.

"Last year 150 people were there. This year Ursula wants 250 so you girls will help Yolanda find the venue. That means checking all the areas in the city and parts of New Jersey for a location that is big enough. So good luck with that and do us proud girls." Rafael replied walking out of the room.

Yolanda approached the other desk in the office and put the rest of the material on it and then walked out of the room.

"This seems like fun and the best part is we get to go." Sienna said while Charlotte was barely hearing her because her phone began to ring at that moment.

"Hello"

"You know it's kinda hard to see each other if the other one never calls." A voice replied huskily.

"Hi Tristan. I've been meaning to call you but between starting school and beginning my internship today I never get the chance." Charlotte replied.

"I get it especially since Michelle said you don't have my number and I put it in her phone. Listen do you think we could have lunch together. Catch up and see where we are in our lives." Tristan said.

Charlotte fidgeted with the lid of the envelope thinking about what to say. "Lunch at 1:30 fine with you?"

"Ok I'll pick you up just text me the address and I'll be there. I can't wait to see you Char. Tristan said hanging up.

Charlotte was confused still about sitting down and having lunch with Tristan. He always had this way of making her feel like she was on a rollercoaster that never stopped.

Sienna looked at her new co-workers face and asked "What's with the face?"

"It is nothing."

"Must be something for you to look like you wanna throw up." Sienna stated smartly.

"Ok here is the thing, I am sitting down with my ex for lunch. I haven't seen him in over two years and I don't know what to expect from him. We've had our high and low moments but he was a good boyfriend overall. Now I am thinking random thoughts in my head about what he wants to talk about." Charlotte rambled and then sighed.

"Girl you won't get your answers with an attitude like that. Just sit down and have a conversation with him. If you don't like what he has to say then tell him to shove it and fuck off. If you think you guys want more than friendship see where it goes and live in the moment. You'll keep questioning yourself if you don't get it over with." Sienna advises Charlotte as Yolanda walks back in.

"Ok girls lets get started on these invitations and then go from there." Yolanda said sitting down while the girls share a small smile with one another.

(Time Skip)

For the next three hours the girls had saw names of celebrities that were invited such as: Anna Wintour, Scarlett Johansson, Ryan Gosling, Beyonce, Adam Levine, & Naomi Campbell to name a few. It was exciting to know that they were going to be in the same room as them.

Yolanda stood up from her desk and looked at the girls. "Ok girls I'm going to a staff meeting and I probably won't see you girls until tomorrow afternoon. We are gonna be pounding the pavement looking for a venue. So be well rested".

"Bye Yolanda" the girls reply as she leaves the office. Sienna then turns to Charlotte with a happy face.

"I can't believe we get to go to one of the biggest parties of the year. Now I'm thinking of what to wear." Sienna said excitedly.

Charlotte grinned at her new friends excitement over the work event. This would be a great opportunity for the girls to network and meet people in the industry. Charlotte's thoughts were soon interrupted by her phone ringing.

"Hello" she answered quickly.

"Hey is this a bad time?" A voice asked huskily.

"Tristan?"

"Yeah"

Charlotte was happy he called her right at this moment. It made it easier for her to ask him to meet up.

"Listen I was wondering if you wanted to meet up and have lunch today? That is if your not busy?" Tristan asked Charlotte.

"I would like that. Let me text u the address and we will go from there." She said.

"Cool see you then." Tristan said hanging up.

Charlotte looked out the office window with a grin and then sent the address to Tristan's phone before returning to the envelopes.

(Time Skip)

Charlotte had left the office to head outside to meet Tristan. She was really anxious to see him with a tinge of nervousness. Soon a silver Porsche pulled up in front of the building with Tristan in the driver's seat. He pulled the car to a complete stop and got out of the car, all the while still looking perfect.

"You always knew how to make an entrance." Charlotte said smartly.

He gave her a smoldering look and opened the passenger door for her. "Well it always kept you talking and that's what mattered" he fired back seeing her smile while getting in the car.

Charlotte watched as he ran to get back into the driver's seat and soon they were pulling off down the street. She watched as he drove the car smoothly through the Manhattan streets like a racecar driver. He turned the radio on and a song began to play:

 _This is where the chapter ends_  
 _A new one now begins_  
 _Time has come for letting go_  
 _The hardest part is when you know_  
 _All of these years - When we were here_  
 _Are ending, but I'll always remember_

 _We have had the time of our lives_  
 _Now the page is turned_  
 _The stories we will write_  
 _We have had the time of our lives_  
 _And I will not forget_  
 _The faces left behind_  
 _It's hard to walk away_  
 _From the best of days_  
 _But if it has to end_  
 _I'm glad you have been my friend_  
 _In the time of our lives_

 _Where the water meets the land_  
 _There is shifting in the sand_  
 _Like the tide that ebbs and flows_  
 _Memories will come and go_  
 _All of these years_  
 _When we were here_  
 _Are ending_  
 _But I'll always remember_

 _We have had the time of our lives_  
 _Now the page is turned_  
 _The stories we will write_  
 _We have had the time of our lives_  
 _And I will not forget_  
 _The faces left behind_  
 _It's hard to walk away_  
 _From the best of days_  
 _But if it has to end_  
 _I'm glad you have been my friend_  
 _In the time of our lives_

 _We say goodbye_  
 _We hold on tight_  
 _To these memories_  
 _That never die_  
 _We say goodbye_  
 _We hold on tight_  
 _To these memories_  
 _That never die_

 _We have had the time of our lives_  
 _Now the page is turned_  
 _The stories we will write_  
 _We have had the time of our lives_  
 _And I will not forget_  
 _The faces left behind_  
 _It's hard to walk away_  
 _From the best of days_  
 _But if it has to end_  
 _I'm glad you have been my friend_  
 _In the time of our lives_  
 _I'm glad you have been my friend_  
 _In the time of our lives_

She continued to stare at him as the song finished. It summed up everything that happened between them. Hopefully they could come to some sort of resolution on where they would stand.

"Are you gonna stare at me the entire time I drive ?" He asked with his eyes still on the road.

"I'm trying to figure out what to say to someone you used to spend every moment together but you don't really to say." She tells him when they stop at a red light with him turning to glance at her.

"You think you're the only one who doesn't know what to say? I've thought about several different scenarios on what I would say to you if I ever saw you again. At this moment I'm just happy were in the same place at the same time." He tells her while continuing to drive while grabbing her left hand and holding it with his right hand.

Charlotte looked down at where there hands connected and thought about their first date and what a night it led to.

 _(Flashback)_

 _It had been two weeks since the birthday debacle at The elder Gilmore's home. Charlotte had been texting Tristan back and forth since then. He had made an effort to see how she was handling things in her day to day life._

 _Then out of the blue he had asked Charlotte out on a date. Now she was rushing home from working a long shift at Luke's. She had not told her mom that she was going on her first date. Charlotte did not want a repeat of Rory's first date with Dean. Lorelai had took it upon herself to invite Dean over there house for movie night._

 _Even though things worked out in the end, to say it was embarrassing for Rory was an understatement. Your first date with your mom and sister said it all. So Charlotte prepped Tristan on things to do and say around her mom._

 _Charlotte had reached the front yard of the house when she saw Lorelai and Rory sitting on the porch with a mug of coffee in each of their hands. They both were staring at her with devious looks on their faces. They knew she was going on a date and now they were going to rub it in her face._

 _"Hi Sweets, how was school today?" Lorelai asked taking a sip of her coffee._

 _"Fine" she replied shortly._

 _"That's not what I heard at school today" Rory added._

 _Charlotte blushed then headed inside the house with both her mom and sister following right behind her. She headed upstairs to her room and could here their footsteps behind her._

 _"So what is this I hear that you my dear have a date tonight?" Lorelai asked._

 _Charlotte mumbled something under her breath and Lorelai put her hand to her ear._

 _"I'm sorry but I can't hear what you are saying. Do you mind repeating that for me" she added._

 _Charlotte sighed and then looked up at her mom "I am going on a date tonight with Tristan Dugrey. No I don't know where we are going. No I don't care if he reminds you of Dad. I want to go out with him because he was actually nice to me at Madame Tussauds house of Gilmore." Charlotte rambled._

 _Lorelai and Rory laughed at Charlotte's discomfort at the situation. Normally she is well put together and nothing really phases her._

 _Charlotte then turned to her sister and said "What did you mean you heard at school?"._

 _"Tristan asked me what you liked because he wants to make a good impression on you. You apparently are not a shallow vapid girl like the ones he normally dates. So you are a new territory for him." Rory told her sister._

 _"That's actually kinda sweet of him to do that" Lorelai adds while Charlotte is in her closet pulling clothes out left to right._

 _"I don't know what to wear" she says diving into her bed head first._

 _Lorelai looked at the clothes that her daughter threw on her bed. She started to sift through them until she found the perfect outfit._

 _"OK, Charlotte I found the perfect thing for you to wear. Now try it on so we can see you in all of your perfection that you are." Lorelai tells her daughter who goes to the bathroom._

 _Forty minutes later Charlotte walks back into her room and she sees her mom and sister eating poptarts on her bed. She approaches them and stands in front of them._

 _"What took you so long?" Lorelai asked with boredom._

 _"I took a shower first so I wouldn't smell like I worked in a diner all day" Charlotte smartly replies to her mother._

 _"So what do you guys think?" Charlotte asked the two._

 _She was wearing a flower print dress with red put her hair in a ponytail and a little bit of make up._

 _"You look pretty sis" Rory said._

 _"Yeah Sweets Tristan will like you just the way you are." Lorelai added._

 _All three of the Gilmores walked out of Charlotte's room and headed downstairs into the living room. Lorelai picked up a magazine and sat on the couch while the girls headed into the kitchen._

 _"So what are you doing tonight Rory? I feel like we haven't spent enough time together since you started Chilton. I mean between me working and you dealing with those rich snobs I miss hanging out with you." Charlotte tells her sister while grabbing a water bottle from the fridge._

 _"Mom rented movies and we're going to pick up food from Luke's." Rory replied._

 _Soon the phone begins to ring and Charlotte ran into the living room. As she walked in she saw her mom answering_

 _"Hello Gilmore Residence. Yes she is, hold on a second" Lorelai says handing the phone to Charlotte._

 _"Hello"_

 _"Hey" Tristan replies._

 _"Hi, are you almost here. If your calling to cancel I understand, I mean you probably have other girls waiting." Charlotte rambles with her mom shaking her head at her daughter's oblivious attitude._

 _"I was actually calling to tell you to look out your living room window. But if you want me to cancel I completely understand. Also just to let you know there are no other girls." Tristan tells Charlotte who is grinning as she opens the window. Charlotte hurried to open the front door and stood on the porch._

 _Tristan is leaning on his Porsche with a bag that says "Luke's Diner". He was dressed in a white collared shirt, dark blue jeans, and a pair of converse sneakers. He got off of his car and walk toward Charlotte. When he was directly in front of Charlotte he took her hand in his and kissed it._

 _"You look beautiful" he told her._

 _"You dont look so bad yourself Dugrey" Charlotte said._

 _Tristan then led her down the porch steps to his car. He opened the passenger door for her and she sat down in the car. When he sat down beside her in the driver seat Lorelai and Rory walked out from the house and on to the porch._

 _"Make sure you get home before ten, Charlotte. It's still is a school night and don't do anything I would do" Lorelai said coyly with Rory laughing at her mom._

 _"Dirty" Rory added with grin._

 _"Don't worry Ms. Gilmore ill bring her home on time." Tristan explained while Lorelai made a face at the ''Ms. Gilmore jab" making her daughters laugh at her._

 _Tristan then started the car and they pulled off leaving Lorelai and Rory as little blimps in his rear view mirror. Charlotte was staring at the road while Tristan would glance at her as he was driving. He was trying to play it cool but when it came to Charlotte he was nervous. She was the first girl who actually liked him for him and not what his last name could do for social standing._

 _"So where are you taking me tonight? I tried to ask Rory but she wouldn't budge." Charlotte said to Tristan breaking him out of his thoughts._

 _"Well Rory told me you like classic movies and a buddy of mine told me there is a drive in movie theater playing 'Casablanca' tonight." Tristan then lifted up the bags form Luke's. "I also asked your sister what's your favorite food. So I went to Luke's and mind you that guy scares me. He glared at me the entire time I was there." Tristan told Charlotte._

 _Charlotte then laughed at the face Tristan made. "The reason he glared at you is probably the fact that you are the first guy to ask me out. Luke is my dad in all but blood and now that he sees I am dating he wants to protect me. Normally I'm the type of person who focuses on other things beside dating. That all changed that night you brought me home from my grandparents. You actually noticed me in that circus and for the first time I actually liked a guy. Charlotte explained._

 _"Well let's just say I am happy you decided to go out with me. I know I have a reputation of being a conceited dick but I am a nice guy" Tristan bluntly adds._

 _"The night is still young so all you have to do is be yourself. I am a average girl so don't try so hard." Charlotte told the boy who released a sigh of relief as he continued driving._

 _Tristan pulled into the drive in theater and found a good spot for them to watch the movie. He then opened up the food and handed Charlotte hers. The movie began and they sat in silence eating. They were both wondering if the other was having a good time. Tristan tried to glance at Charlotte from the corner of his eye. She was watching the movie and miming the words from the scene._

 _Charlotte although she was watching the movie she knew Tristan was trying to watch her. In her head it was kinda flattering. A guy has never paid this much attention to what she was doing. If they were she never noticed them._

 _"Are you enjoying the movie?" he asked_

 _Charlotte continued to stare at the movie and then took a sip of her soda before glancing at Tristan with smile. "I am and the company ain't so bad either." She replied._

 _Tristan grinned and held out some candy out towards her and she smiled and took some. For the rest of the night the two enjoyed each others company. When the movie ended Tristan saw they still had and hour left to hang out._

 _"So I was thinking do you want to grab a coffee before I bring you home?"_

 _"I'd like that." She said turning to him and added "When are you gonna kiss me?"_

 _Tristan was kind of shocked at the question. He knew Charlotte and her sister were different people. So he assumed when it came to dating they would have the same feel for how they want their first kiss. It kinda threw him off for a moment and then he leaned in. For Charlotte, this was her first kiss and it was perfect._

 _When Tristan pulled away from Charlotte she blushed and looked away from him making him smirk. He then turned on the car and drove out of the movie theater._

 _After getting them coffee and talking some more Tristan pulls up in front of Charlotte's house. He turned off the car and turned to face Charlotte. She was sitting next to him with her hands in lap and she was looking at her house._

 _"Did you have a good time tonight?" Tristan asked the girl._

 _"I had a great time tonight Tristan. For a first date it was perfect in my opinion. Like I said before you don't have to try so hard to impress me."She explained leaning over and kissing Tristan on the cheek and slowly got out of the car._

 _Tristan place his hand on were her lips touched his cheek. He looked up expectantly at the girl as she walked to her porch. Tristan then got out of the car and grabbed Charlotte's arm making her turn to face him. Charlotte faced him and his face met hers in another kiss._

 _While the couple was kissing they didn't see Lorelai watching them in the living room window with a small smile on her face._

 _(End Flashback)_

Eventually Charlotte noticed they had pulled up in front of small bistro and Tristan had already opened her door. He was watching her smugly as she stepped out of the car heading for the bistro. The waiter soon escorted them to their seats and then took their order before leaving them alone.

Tristan placed his hand on Charlotte's from across the table and glanced at her. "I'm glad you decided to have lunch with me, Char".

Charlotte pulled her hand away from his and got straight to business. She had questions and he had the answers and she needed them now.

"I was against it mostly but I figured if I can actually sit down with you, maybe I would get the answers I need." Charlotte said.

"What do you want to ask me Charlotte? Don't hold your tongue on my I account." Tristan said.

"Was I a good girlfriend to you?" She asked him.

"Where is this all coming from Charlotte? I thought you wanted to catch up and reminisce with me about the good times" He said irritably.

"In order for me to do that I need closure from the situation. You left and I never got say what I really wanted to say to you. I loved you but between the pressure of your family and whatever else you were going through, you pushed me away from you." She said with tears rolling down her face.

Tristan looked at the girl sitting in front of him. He could see all the pain he caused her and how she still held some of it. She had pulled out some napkins from her purse and wiped her face. He knew she at least deserved a chance to move on from the past.

"You were a good girlfriend. The best. At that time I couldn't see it because I didn't know what I wanted," Tristan finally spoke up. "I was a stupid kid trying to prove something to people around him. You were the only good thing in my life and I didn't want to drag you into it."

Charlotte looked at the sincere face he had on. If she were her sixteen year old self she would have told him it was ok. In that moment Charlotte knew what she had to say to him.

"I forgave you along time ago cause I know I made it hard for you to talk to me. When you left I blamed myself and for weeks I was angry. I took it out on my mom, Rory, Michelle, and Luke. I just needed you and I felt alone."

"Once again I'm sorry for everything. I mean it Charlotte, you never deserved any of it. I want us to start over and try to be friends and maybe something more later. That is if you think that could happen between the two us.

Charlotte agreed with him and thought over everything he just said. He had acknowledged his part in why there relationship fell apart but there was still one thing she needed to get off her chest.

"One more thing before put this to rest. What were you thinking when you kissed Summer at that party?" She asked curiously taking a sip of her water.

"That night was that party right," he asked in which she nodded. "You and I just had this big fight about how I don't open up. I was drunk and I know it doesn't justify it but it happened. Summer even said it shouldn't of happened."

"Ok"

"That's it, nothing else we need to talk about?"

"That is everything I needed to know at this moment. I'll let you know if there is anything else that comes to mind." She said when the waiter returned.

Soon the waiter returned with their food and the two old friends caught up on what had changed in their lives. In Tristan's case he talked about him graduating from military school and going to Columbia University to study law. He also found a place in the Upper East Side. Charlotte had also caught him on what had changed in her life since he had left.

"Wow I knew me leaving would change things in your life." Tristan said.

"Well your hear now and that is what counts." Charlotte said.

(Time Skip)

After they had finished their food Tristan paid for their meal. He grabbed her hand in his and they left the bistro and got in his car. The ride was silent but it wasn't awkward for them. It was a comfortable silence for the two after the conversation they had.

Tristan looked over at the girl and saw her staring at the New York Streets as they drove back to Underwood Designs. She was deep in thought and he had to know if she still wanted him apart of her life as a friend or more.

"So have you decided on what I asked?" Tristan asked

"I think I agree with you on friends first and then more later on" She replied.

Tristan was happy at least he could be something in her life to some capacity.

Tristan's car pulled up in front of Charlotte's job. When she tried to get out of the car he grabbed her hand. Charlotte turned to face him and saw a smile on his face. She looked closely and saw there was a twinkle in his eyes.

"What is it?" She asked.

"We should do this again sometime. If we are gonna try being friends then we should try to hang out. Don't you think?" He asks.

"I would like that a lot. So I will call you and we can plan something. Well I have to go back to work." Charlotte said eventually getting out of the car.

She walked towards the entrance of the building and turns around to look back at Tristan. He was watching her and he was smiling at her. Then he waved and drove off down the street speeding away. Charlotte turned around and walked inside and headed back upstairs. When she walked into the office only Sienna was there.

"How was lunch with the ex?" Sienna asked when she noticed Charlotte walk in the office.

"Emotionally draining. I got my answers to most of my questions but something still feels like it needs to be said." Charlotte explained while getting back to work.

Sienna walked over to the copy machine and placed something in the machine. "Well you just had lunch with him. Let it resonate with you first then think about what you still need answered. Otherwise it will keep stirring up old emotions." Sienna told Charlotte.

"Hey quick question, what are you doing tonight?" Charlotte asked her new friend.

Sienna thought about it for a minute. "Nothing really, why?".

"Well my neighbor is throwing a party and he said I could invite anyone. So I figured since you just moved here and you don't know anyone you could have fun with me and my friends." Charlotte said.

"Thanks that could be fun. Can we stop by my apartment first so I can get an outfit and then go to yours?" Sienna asked.

"Yeah, I actually got to call my roommate and my friend from school to see if there going still. Tonight should be fun this is my first party in New York. So why not live in the moment." Charlotte said placing the envelopes on her desk in a box.

As the girls were working Rafael walked into the office and Yolanda followed him right after. Rafael saw the girls were practically done with all the work he had assigned them. He was impressed and that was not something he gave lightly.

"Girls, we have a staff meeting and Ursula would like for you to attend. She wants you two to get a feel of how things operate here. So would you please follow me to the boardroom. The meeting is about to begin. Charlotte picked up a notepad off her desk and followed after Sienna who was following both Rafael and Yolanda.

When they reached the boardroom everyone was taking their seas while the girls stood to the side close to the exit. Ursula sat at the lead chair and looked irritated at everyone. Rafael sat two seats away from Ursula on her left and he was nervous about something.

"Now that all of you are here can we finally get things underway. I have an appointment to get too and you are all wasting my time." She said standing up from her chair pacing.

"Well Vogue wants you to sit down and have an interview and talk about the Gala event and what to expect. Like what are we displaying this year and how it will differ from others". One of the workers said.

"Setup a time with my assistant and let me know when everything is scheduled" Ursula ordered.

Ursula then looked at the interns on the wall before looking at Rafael. "Are the invitations ready to go out? What about the venue? I would hope you have some good news to tell me Rafael." Ursula asked earnestly.

"Well the girls finished all the invitations just before we came here. Sienna already printed out a list of locations for the gala to be held. Yolanda and the girls are going to be checking each one to see if they fit the requirements you requested." Rafael said to Ursula.

"Fantastic! What about the designers who will be showcasing their work. I need at least twenty-five to thirty designers to have a custom design ready." Ursula urged to her staff.

"We have scoured around the city and the surrounding areas and so far we have fifteen designers." Another worker added.

Charlotte saw the facial expression on Ursula's face and she had an idea. Hopefully the idea wouldn't be shot down.

"Excuse me Mrs. Underwood. I have an idea and I wanted to run it by you and the rest of the staff." Charlotte said surprising everyone in the room.

"This ought to be good" a coworker said snidely.

"Miss Gilmore, what is this idea you have that nobody else in this room doesn't have?" She asked bored and a bit curiously.

"Well as you know I go to FIT and there are hundreds of designers who go to my school. Why not hold a fashion exhibition and the fifteen designers Ursula likes will have their design showcased at the gala event." Charlotte explained her idea to everyone.

Ursula looked at the girl in front of her. She had just interviewed her this morning and already she was pitching ideas in her staff meetings. Ursula would have to watch this girl closely.

"How would we go about promoting this plan at the school?" Ursula asked Charlotte.

Charlotte walked up to the front of the boardroom and stood next to Ursula. " You could speak to someone at the school and set it up so it could happen within the week. Unless anyone of you have any great ideas?" Charlotte asked the other men and women in the room smugly.

"I like it and I want it done within the week. Charlotte i want you to speak to Harper Spaulding. He will help you with whatever you need. Now Meeting adjourned, I have places to go, people to see." Ursula said walking out the room with people following her.

"That was so scary. You just pitched an idea on your first day to practically everyone who works here." Sienna said excitedly rushing over with Rafael behind her.

"You've got guts girl. It took me eight months to pitch an idea when I started working here." Rafael added walking out with Sienna trailing right after him.

Charlotte smiled at the praise her new coworkers gave her. It gave her the confidence she really needed. She walked out of the boardroom only to walk into someone.

"I am so sorry I didn't see you." Charlotte explained apologetically.

"It's fine" the man said picking up the papers he dropped. Charlotte helped him pick up the papers.

He then rushed off down the hallway away from Charlotte. Charlotte shook her head and headed back to the office she shared with Sienna. When she got there Yolanda was walking out and said "I will see you girls on Monday because we will be walking to different places too see where the gala can be held. Bye girls."

Charlotte went to her desk and put on her jacket and picked up her purse. She then looked over to her new friend. "Hey you ready to go to your apartment so we can get your stuff?"

"Yeah let me just get my bag then we can go" Sienna replied.

Charlotte and Sienna both left the office and walked pass the other workers. Some of them were glaring at Charlotte with jealousy from the staff meeting earlier. Charlotte didn't care to be honest, she was happy that Ursula liked her idea enough to go through with it. The girls walked downstairs into the lobby of the design house and saw Rafael talking to the guy Charlotte had walked into earlier.

Rafael looked there way and waved to them. They both headed to him and he began introductions. " Ladies I would like for you to meet Harper Spaulding. He basically runs the day to day operations here at Underwood Designs."

"I've met this one Rafael she bumped into me earlier. I don't believe I got your name either." Harper said.

"Charlotte. Charlotte Gilmore" She said with her hand raised to shake his.

He shook it then turned to Sienna "And your name miss?"

"My name is Sienna Miller."

"Well ladies it was nice to meet you but I have a prior engagement I am late for." He said walking away before turning around. "Charlotte, Ursula wants for you to come up with a plan so on Tuesday meet me in my office." Harper adds before walking away.

Rafael then says his goodbyes to the girls and walks out of the building as well.

"Well how are we getting to your apartment Sienna?"

"My car is parked around the corner. My mom told me I was crazy for driving across the country with my car. I told her it beats taking the bus. But I will say this, finding parking anywhere in this city is unbelievable." Sienna rambled a bit as they got in the car.

"Well let's head to your place and you can pack a bag and stay the night at mines so you won't have to drive so late." Charlotte offered.

"Sounds like a plan" Sienna said starting the car.

(Time Skip)

After the girls had packed a bag at Sienna's apartment they went straight to Charlotte's apartment. They were now entering the lobby when Mr. Jones came towards them.

"Good evening Ms. Gilmore, you have a friend waiting for you in the waiting area." He said pointing to Ethan who was on his phone.

"Thanks Mr. Jones." Charlotte said walking over to Ethan with Sienna right behind her.

When she got in front of him he looked up from his phone and saw her. He wasn't paying attention to Charlotte though. Ethan was staring at Sienna with a look that she had seen with men only around her mom. The look that they glanced at her but had to see if she was really there.

"Hi Ethan" Charlotte said waving in his face to gain his attention back on her.

"Char, hey. How are you? Who's your friend?" Ethan asked shyly while still staring at Sienna.

Sienna walked over to Ethan and smiled sweetly. "Hi my name is Sienna. I work with Charlotte over at Underwood Designs." she said.

"Not that introductions aren't nice I think we should go upstairs and get ready." Charlotte added making her friends blush with awkwardness.

Charlotte led her friends to the elevator waving to Mr. Jones when the doors opened. She pressed the number six on the panel when they all stepped in. As the elevator ascended Ethan kept making small little glances over to Sienna who was doing the same. Charlotte on the other hand was thinking about how she was gonna plan the exhibition at her school.

The elevator door opened on the sixth floor and the friends walked down the hallway. As they were walking down the hallway Austin's apartment door was opened. They saw him and two other guys moving the furniture around in his apartment.

"Ok guys just put the couch there while I setup the drinks" Austin said running to the kitchen.

Charlotte walked pass his apartment and pulled her keys at out her purse. She put her keys into her apartment door and saw Michelle in the living room watching TV. Ethan and Sienna walked in right after her.

"Hey Chica how was your first day?" Michelle asked turning off the TV.

"Good. Michelle I would like for you too meet my new friend Sienna. She works with me at Underwood Designs." Charlotte answered.

Michelle got up and hugged Sienna surprising her. "Hi it's nice to meet you. Make yourself at home here." She said.

"So what time are you girls gonna get ready for the party?" Ethan asked.

Well I already know what I'm wearing. What about you guys?" Sienna asked the roommates.

Michelle walked into her room and came back out with a pair of white jeans and a black blouse, a air of stilettos. "I had my outfit picked out along time ago. When Char first told me about the party I wanted something that would keep the attention on me. "Michelle said provocatively making the girls in the room laugh while Ethan blushes.

"I still need to pick out something so why don't you guys hang out for a bit. Sienna you will be sleeping in my room tonight and Ethan the couch is yours." Charlotte said going into her room.

While Charlotte is looking for something to wear when her cell phone rings. She walks out of her closet and sees it is her mom. She smiles shortly and realizes she hasn't spoken to her mom in days. She picks up the phone and sees a voicemail so she listens.

 _"Fruit of my loins its mommy. I haven't heard the sound of your voice in eons. Please call mommy so she can know you are alive. Also are you coming home this weekend cause your sister is. I wanna know how school and the internship is going. Call me when you get the chance." Lorelai said_.

Charlotte looked down at her phone and thought maybe tomorrow she could go down to Stars Hollow and visit her mom and sister. While Charlotte was contemplating her weekend plans Michelle, Sienna, and Ethan walked into her room unnoticed.

"Charlotte why are you staring at your phone like that?" Michelle asked.

"My mom called and I realized I haven't spoken or thought of her for a while. So I was thinking can I borrow your car for the weekend and drive out to Stars Hollow. If not I'll take a Greyhound Bus." Charlotte said to her best friend.

"Sure. Whatever you need, all I ask is you fill her up on the way back." Michelle said cheekily.

"So what are you gonna wear?" They all asked Charlotte. In which she gave them a small smile.

(Time Skip)

Michelle, Ethan, and Sienna walked out of the apartment with Charlotte coming out last to lock the door. She was dressed in a short black dress with knee high boots. She had also curled her hair. They walked down the hallway hearing the music vibrating on the the group stopped in front of Austin's apartment Charlotte knocked on the door. They waited until Austin himself opened the door.

"Hey Charlotte you came." He said with grin looking her up and down.

"Well you invited me and I didn't want to be rude. These are my friends Michelle, Sienna and Ethan." Charlotte said introducing her friends.

"Hey come on in the party has already started. There is food and drinks so help yourself." Austin said leading them into the party before walking to some girl with a red cup in her hand.

"You heard the guy lets party" Michelle said as a guy walked pass them with a guitar.

Sienna's nearly eyes popped out of her head when she got everyone's attention. "Guys isnt that Pete Wentz of Fall Out Boy?" Sienna asked fanning out.

Charlotte and Michelle both looked closely and turn to her "Yes!" They said excited.

"Please don't tell me you guys are groupies" Ethan said shaking his head at his friends making them glare at him. He put his hands up in defense. "I am just stating my opinion especially because of your reactions" he added.

Soon the girls saw the rest of the band join him on the balcony. Austin took a microphone and began speaking. " I wanna thank my boy Pete Wentz for gracing us his presence tonight at my party. So ladies and gentlemen I give you Fall Out Boy." Austin announced.

"Thanks Austin. Now i know everyone knows this song" Pete said.

 _She says she's no good with words but I'm worse_  
 _Barely stuttered out a joke of a romantic stuck to my tongue_  
 _Weighed down with words too over-dramatic_  
 _Tonight it's "It can't get much worse"_  
 _Vs. "No one should ever feel like..."_

 _I'm two quarters and a heart down_  
 _And I don't want to forget how your voice sounds_  
 _These words are all I have so I'll write them_  
 _So you need them just to get by_

 _Dance, dance_  
 _We're falling apart to half time_  
 _Dance, dance_  
 _And these are the lives you love to lead_  
 _Dance, this is the way they'd love_  
 _If they knew how misery loved me_

 _You always fold just before you're found out_  
 _Drink up it's last call,_  
 _Last resort_  
 _But only the first mistake and I..._

 _I'm two quarters and a heart down_  
 _And I don't want to forget how your voice sounds_  
 _These words are all I have so I'll write them_  
 _So you need them just to get by_

 _Why don't you show me a little bit of spine_  
 _You've been saving for his mattress, love_

 _Dance, dance_  
 _We're falling apart to half time_  
 _Dance, dance_  
 _And these are the lives you love to lead_  
 _Dance, this is the way they'd love_  
 _If they knew how misery loved me_

 _Why don't you show me a little bit of spine_  
 _You've been saving for his mattress (mattress, mattress)_  
 _I only want sympathy in the form of you crawling into bed with me_

 _Dance, dance_  
 _We're falling apart to half time_  
 _Dance, dance_  
 _And these are the lives you love to lead_

 _Dance, this is the way they'd love (way they'd love)_  
 _Dance, this is the way they'd love (way they'd love)_  
 _Dance, this is the way they'd love_  
 _If they knew how misery loved me_

 _Dance, dance_  
 _Dance, dance_  
 _Dance, dance_  
 _Dance, dance_

Then the band played:

 _I'm gonna make you bend and break_  
 _(it sent you to me without wings)_  
 _Say a prayer but let the good times roll_  
 _In case God doesn't show_  
 _(let the good times roll, let the good times roll)_  
 _And I want these words to make things right_  
 _But it's the wrongs that make the words come to life_  
 _"Who does he think he is?"_  
 _If that's the worst you got_  
 _Better put your fingers back to the keys_

 _One night and one more time_  
 _Thanks for the memories_  
 _Even though they weren't so great_  
 _"He tastes like you only sweeter, "_  
 _One night, yeah, and one more time_  
 _Thanks for the memories, thanks for the memories_  
 _"See, he tastes like you only sweeter."_

 _Been looking forward to the future_  
 _But my eyesight is going bad_  
 _And this crystal ball_  
 _Is always cloudy except for (except for)_  
 _When you look into the past (look into the past)_  
 _One night stand (one night stand off)_

 _One night and one more time_  
 _Thanks for the memories_  
 _Even though they weren't so great_  
 _"He tastes like you only sweeter."_  
 _One night, yeah, and one more time_  
 _Thanks for the memories, thanks for the memories_  
 _"See, he tastes like you only sweeter."_

 _They say I only think in the form of crunching numbers_  
 _In hotel rooms collecting page six lovers_  
 _Get me out of my mind and get you out of those clothes_  
 _I'm a liner away from getting you into the mood, whoa_

 _One night and one more time_  
 _Thanks for the memories_  
 _Even though they weren't so great_  
 _"He tastes like you only sweeter."_  
 _One night, (oh!) yeah, (oh!) and one more time_  
 _Thanks for the memories, thanks for the memories_  
 _"See, he tastes like you only sweeter."_

 _One night and one more time (one more night, one more time)_  
 _Thanks for the memories_  
 _Even though they weren't so great_  
 _"he tastes like you only sweeter." (oh)_  
 _One night, yeah, and one more time (one more night, one more time)_  
 _Thanks for the memories, thanks for the memories (thanks for the memories, thanks for the memories)_  
 _"see, he tastes like you only sweeter." (oh)_

After the band finished that song they took a break. Charlotte saw Ethan and Sienna sitting on a couch in the living room. She looked around for Michelle and saw her in the kitchen chatting to a guy about business and something else. She walked over to the balcony rail and looked at the city skyline.

"It's a nice view ain't it." Austin said from behind her.

Charlotte turns around to face him and she sees him hold two red plastic cups. He holds one out to her. "Here I figured you be thirsty" he adds.

"Thanks. What is it?"

"Its Sprite. Well I figured you might be a minor and I can tell you don't drink." he cautiously said.

"You figured right. So I wanna know something how do you know Fall Out Boy?" She said.

"I am a A&R Exec here in New York. I go talent searching every weekend looking for new artists. Maybe you could come with me sometime if your not busy." Austin offered.

"I'll think about it. Well I have to go now if I want to get on the road." Charlotte said walking pass Austin.

"Where are you going if you don't mind me asking?" He asked.

"Home" Charlotte said walking away from him. She walked up to Michelle in the kitchen. "Hey I am leaving early so I can get on the road. I will call you when I get to my moms. Tell Sienna she can sleep in my bed and remind Ethan the couch is his." Charlotte said hugging her best friend.

Charlotte walked out of the kitchen and headed for the apartment door as she grabbed the handle a hand went over hers. She looked over her shoulder and saw it was Austin's.

"Can I help you?" She said.

"When you get back to the city do you wanna go out with me?" he asked.

"Um... Can I think about it and get back to you." She said anxiously trying to leave.

"Sure" he said.

Charlotte opened the door in a rush and walked fast to her apartment.

(Time Skip)

Charlotte had packed a bag of clothes and took her homework and work projects with her as well. She was driving on the Interstate in Connecticut. She had left New York two hours ago and she just wanted to see her mom. Especially since Tristan wants to be more than friends and she was asked out by Austin. She just needed an outside perspective and her mom's always gave her more to think about.

Charlotte played with the radio until a song that every time she thought of Tristan began to play:

 _I would have given you all of my heart_  
 _But there's someone who's torn it apart_  
 _And he's taken just all that I have_  
 _But if you want I'll try to love again_  
 _Baby, I'll try to love again, but I know..._

 _The first cut is the deepest_  
 _Baby I know_  
 _The first cut is the deepest_  
 _But when it comes to bein' lucky, he's cursed_  
 _When it comes to lovin' me, he's worst..._

 _I still want you by my side_  
 _Just to help me dry the tears that I've cried_  
 _And I'm sure gonna give you a try_  
 _If you want I'll try to love again, (try)_  
 _Baby, I'll try to love again, but I know..._

 _OOHHH,_  
 _The first cut is the deepest_  
 _Baby I know_  
 _The first cut is the deepest_  
 _But when it comes to bein' lucky, he's cursed_  
 _But when it comes to lovin' me, he's worst..._

 _I still want you by my side_  
 _Just to help me dry the tears that I've cried_  
 _But I'm sure gonna give you a try_  
 _Cuz if you want I'll try to love again_  
 _(Try to love again, try to love again)_  
 _Baby, I'll try to love again but I know, OOHHH..._

 _The first cut is the deepest_  
 _Baby I know_  
 _The first cut is the deepest_  
 _When it comes to bein' lucky, he's cursed_  
 _When it comes to lovin' me, he's worst_

 _OOHHH, the first cut is the deepest_  
 _Baby I know (baby I know)_  
 _The first cut is the deepest_  
 _Try to love again..._

When the song finished Charlotte realized she was in front of the crap shack. She grabbed all her stuff from the car and saw the tv on in the living room window. She opened the front door and walked in the foyer of the house. Soon footsteps came close to her and her mom and Rory were in front of her.

"Sweets your home" Lorelai said pulling both her daughters into a hug. 

*The next Chapter will be titled _"Chicken or Beef"_ after the Fourth Episode of the Fourth Season. It will be posted Mid- February.

*Charlotte is gonna have a love triangle with Austin and Tristan

*The song(s) are as follow:

 _"Time of Our Lives" by Tyrone Wells_

 _"Dance, Dance" by Fall Out Boy_

 _"Thnks Fr Th Mmrs" by Fall Out Boy_

 _"The First Cut Is The Deepest" by Sheryl Crow_

Chaz746


	8. Chicken or Beef?

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS**

The Life & Times of Charlotte Gilmore Chapter 7: Chicken or Beef?

 _(Previously on The Life & Times of Charlotte Gilmore)_

 _(Time Skip)_

 _Charlotte had packed a bag of clothes and took her homework and work projects with her as well. She was driving on the Interstate in Connecticut. She had left New York two hours ago and she just wanted to see her mom. Especially since Tristan wants to be more than friends and she was asked out by Austin. She just needed an outside perspective and her mom's always gave her more to think about._

 _Charlotte played with the radio until a song that every time she thought of Tristan began to play:_

 _I would have given you all of my heart_  
 _But there's someone who's torn it apart_  
 _And he's taken just all that I have_  
 _But if you want I'll try to love again_  
 _Baby, I'll try to love again, but I know..._

 _The first cut is the deepest_  
 _Baby I know_  
 _The first cut is the deepest_  
 _But when it comes to bein' lucky, he's cursed_  
 _When it comes to lovin' me, he's worst..._

 _I still want you by my side_  
 _Just to help me dry the tears that I've cried_  
 _And I'm sure gonna give you a try_  
 _If you want I'll try to love again, (try)_  
 _Baby, I'll try to love again, but I know..._

 _OOHHH,_  
 _The first cut is the deepest_  
 _Baby I know_  
 _The first cut is the deepest_  
 _But when it comes to bein' lucky, he's cursed_  
 _But when it comes to lovin' me, he's worst..._

 _I still want you by my side_  
 _Just to help me dry the tears that I've cried_  
 _But I'm sure gonna give you a try_  
 _Cuz if you want I'll try to love again_  
 _(Try to love again, try to love again)_  
 _Baby, I'll try to love again but I know, OOHHH..._

 _The first cut is the deepest_  
 _Baby I know_  
 _The first cut is the deepest_  
 _When it comes to bein' lucky, he's cursed_  
 _When it comes to lovin' me, he's worst_

 _OOHHH, the first cut is the deepest_  
 _Baby I know (baby I know)_  
 _The first cut is the deepest_  
 _Try to love again..._

 _When the song finished Charlotte realized she was in front of the crap shack. She grabbed all her stuff from the car and saw the TV on in the living room window. She opened the front door and walked in the foyer of the house. Soon footsteps came close to her and her mom was in front of her._

 _"Sweets your home" Lorelai said pulling her daughter into a hug._

As soon as Lorelai let her daughter out of the hug she noticed Charlotte's face. She wasn't her normal upbeat self. Lorelai had seen that look a thousand times on her own face. That face had always been accustomed to boy trouble. She grabbed her daughter's hand and led her to the kitchen. She grabbed two coffee mugs out of the cabinet and poured their elixir of life. She handed Charlotte her mug and sat down next to her.

"Do you want to tell me why you drove straight here in the middle of the night? I spoke to Michelle earlier, she told me you guys were going to a party tonight." Lorelai said without breathing.

"I realized I missed you." Charlotte told her mother who gave her a smile in return.

"I know sweets. I want you to realize that even though we don't see or speak to each other everyday doesn't mean we don't think about one another." Lorelai said wisely.

"Thanks Mom. But there is another reason I came here. I had lunch with Tristan yesterday and we spoke but I still feel like there are things to be said. At the moment I have to think about those things before I can just jump into a relationship with him. So for now we are trying to be friends." Charlotte said.

"That is a good way to think about things Char. Like I told you before do you think your ready to be in a relationship with Tristan again?" Lorelai said.

"I don't know" she said drinking her coffee.

Lorelai gets up and goes into the cabinet and pulls out a box of poptarts and offers her daughter one. "You can't think clearly without some brain food." She reasons with a devious grin making Charlotte laugh.

"I also need to tell you something but I don't want you telling Rory until you think she is ready." Charlotte ominously said changing the mood of the conversation.

"What is it, Charlotte?" Lorelai asks.

Charlotte hesitated before finally saying "Jess isn't in California."

Lorelai looks confused for a moment before getting a little agitated. "What do you mean he isn't in California?"

"Well after my first day of school I ran into him in Washington Square Park. He is not in a good place in life right now. It's like he is afraid to let people close to him without them hurting him at the same time." Charlotte explained to her mom.

"He broke Rory's heart and I know he didn't have the greatest upbringing but that doesn't give him the right to treat anyone the way he feels like." Lorelai replies unhappily.

Charlotte was tired of her mom having this negative attitude towards Jess. Granted he disrespected her when he came over for dinner.

"The sad part is you and Jess are just alike mom. Except he wasn't as strong as you are. Instead of judging him you should try to get to know him better." Charlotte states to her mom while getting up and heading for the stairs leaving her mom to think about her daughter's words.

(Time Skip)

The next morning an alarm rings throughout the house waking Charlotte from her sleep. She grumbles as she heads downstairs into the living room. She sees her mom and Rory talking by the front door. Lorelai struggled to turn off the alarm with Rory debating with her on Kirk's sanity. When she walks up to the two of them Rory notices her sister and rushes over to hug her.

"Charlotte what are you doing home? I thought you'd be living it big in the city." Rory said to her sister as the three of them sit in the living room.

"Well I missed mom so I figured why not see her while I have free time before work and school take off and I'm busy. How've you been?" She tells her sister.

"Well schools been great and Paris and I are living together. I got asked out recently and it was weird but I guess moving on won't be so bad" She said sadly at the end.

"Take your time Rory." Charlotte said supportively.

Lorelai looks at the interaction of her daughters and thinks about the conversation from last night. She realized Charlotte was right about the similarities between Jess and herself. It was harder for her to acknowledge these things because Jess hurt Rory and she didn't want to sympathize with him.

As they move the alarm goes off once more making all three of them wince in annoyance.

"Its motion sensing" Lorelai exclaims making her daughters give her a look "Really Mom".

"Remind me to hit Kirk with my softball bat when I see him" Charlotte remarked getting a disapproving stare from Rory while Lorelai laughed.

Charlotte shook her head and headed into the kitchen. She pulled open the fridge and saw nothing to eat. She didn't know why she was surprised. She closed the fridge and walked back into the living room.

"Who wants to go to Luke's" Charlotte asked getting a two identical smiles from her mom and sister.

(Time Skip)

The Gilmore girls walked into the town square heading for Luke's. Charlotte had missed the grumpy diner owner who fed them over the years. As they walked further through town they saw men putting boxes on the gazebo. Charlotte and Lorelai ignored the men and headed straight for the diner while Rory went towards the gazebo.

When they entered the diner they saw a table available and sat down. Charlotte looked at her mom and decided to ask her for more advice.

"Mom can I ask you something?" Charlotte asked unsurely.

Lorelai turned to her daughter when she heard the unsure tone in her voice. "Sure, sweets you can ask me anything."

"How do you chose between two guys? I mean on one hand I have a guy I have known for two years and we dated and that spark you feel when your with them is still there. While on the other hand there is another guy who is kinda older than me but it is a new experience. "she tells her mom confused while looking at the menu.

Lorelai in this moment knew her daughter was growing up even more. Charlotte had always put relationships in the back of her mind. She and Rory were alike in that aspect Lorelai thought.

"What brought this on Charlotte? Besides Tristan who is this older guy?" Lorelai asked.

Charlotte then proceeds to tell her mom all of her encounters with Austin up until the party. Lorelai on her part listens then asks "Although I don't like the fact that he is older than you. Do you see yourself dating him if you don't want to be with Tristan?"

"I barely know the guy but he asked me out and I want to see where things go. But I also want Tristan in my life. I know I can't have both so I have too see things play out." She says ending the conversation as Luke comes over.

"Hey Charlotte I didn't know you would be home for the weekend. Hows New York? Is school going well? Are there any guys giving you trouble?" Luke questions.

"Wow Luke you fired questions like Mom. Maybe she is rubbing on you after all. Charlotte said making him blush while her mother grins.

"Ha Ha Ha" He grumbles.

"To answer your questions, I was feeling a little homesick and I missed mom. School is going great and I love New York City. As of right now no guys are giving me trouble unless you count dating" She states nonchalantly.

"You girls are crazy" He states walking away from their table.

Rory walks into the diner with a shocked look on her face. Charlotte glances at her sister and asks "What's with the face?"

"I overheard Lindsay and her mom by the gazebo. Lindsay and Dean are getting married here in the town square this weekend. The men that we saw earlier are setting it up as we speak." Rory said as Luke came with three coffee cups.

When it came to Dean, Rory still wanted to be friends with him even after the whole Dean/Rory/Jess situation. Charlotte minded her business when it came to Dean seeing as she was friends with Lindsay.

"That's great I'm happy for them" Charlotte said.

"Well I have a lot to do today girls. So you too catch up while I run my errands" Lorelai said kissing her daughters cheeks, waving to Luke as s

"So what are you gonna do today Char?" Rory asked her sister.

"I have a lot of work to finish for school and work. I gotta talk to Luke about something and call Michelle later and see how everything is going in the apartment." Charlotte said.

"Well I am going to Lane's to catch up. I will see you later." Rory says walking out of the diner.

Charlotte walked up to the counter where Luke was serving people food. She sat down and waited until he wasn't so busy. Eventually Luke noticed her and stopped what he was doing.

"What's up?" He said putting a towel over his shoulder.

"Have you spoken to Jess recently?" She asked.

"No." He said sadly.

"I saw him earlier this week in the city and he looks so lost. I know he is not the easiest person to deal with but he needs someone in his corner right now. When I saw him it was like the first day he came to Stars Hollow." Charlotte said.

"I don't know what to tell you Charlotte. Jess has always had this wall up and I have tried to help him. I can only do so much until even I have to give up." Luke said sadly.

"Everyone else may have given up but I haven't. He is one of my good friends and I don't abandon my friends in their time of need. I'll see you later" Charlotte said leaving the diner with Luke contemplating the words she spoke.

As she was leaving the diner Charlotte heard someone call her name. She turned around and saw Lindsay running to her with a smile. She ran to meet her and they both hugged.

"I thought you were in New York?" Lindsay asked.

"I'm came home to unwind from the city for a bit. It gets too much after awhile and I missed my mom." She said to her friend.

"Well this is just perfect for me. Listen one of my cousins can't make it to my wedding and I was hoping you would take her place as one of my bridesmaids. Your like the only friend I have in this town and it would mean so much to me" Lindsay asked hopefully.

Charlotte was put in an awkward place with Lindsay asking her to be in the wedding. She would like to be in the wedding to support her friend but she had stuff to do for school and work. Also she knew Rory would have a problem with her being in the wedding party. Underneath all that support Rory was really not happy with Dean marrying young. She wanted him to live his life and go to school.

"I'm sorry Lindsay bit im gonna have to decline. I know we are friends but it's kind of last minute. I also came home to finish a lot of work from school and work. I hope you understand." Charlotte explained.

"I understand it was good seeing you Charlotte. Maybe next time your in town we can go out for coffee or something." Lindsay said hugging her friend once more before walking away.

Charlotte watched as her friend walked away before heading home.

(Time Skip)

After being awkwardly asked to be a bridesmaid in Dean & Lindsay's wedding, Charlotte went back to the crap shack. For three hours she worked on the proposal for the fashion exhibition that she was presenting to the school and Ursula. Her eyes were tired from staring at computer screen for so long and she needed a break.

She picked up her phone and saw a missed phone call from Michelle. She called and waited until she responded.

"Hello" She said with a groggy voice.

"Michelle were you sleeping? I'm sorry for waking you, I missed your phone call from earlier." Charlotte said.

"It's ok chica. I came home an hour ago from the gallery. Sienna and Ethan came for a bit and I showed them around. We made fun of the snobby upper east side crowd. How's Stars Hollow? Michelle asked.

"Good for the most part. Mom and I talked about my dating life, Jess, and Dean and Lindsay are getting married this weekend." Charlotte said listing everything fast.

"What was that last one and say it slowly." Michelle said

"Dean and Lindsay's wedding is this weekend. It feel like they are rushing it to be honest. Also Lindsay asked me to be her bridesmaid." Charlotte said. Right after she had said that Michelle started laughing and she heard sound in the background.

"Are you ok?" SHe asked her friend concerned.

"Yeah I fell out of my bed after that. What did you say? Please tell me her facial expressions when you told her no." Michelle said

"It was just awkward to me to be honest. First of all if I was your friend you would of sent me an invitation earlier or tell my mom. She was sad that I declined but it is what it is." Charlotte told her friend.

"So what's the plan for tonight? Are you having a movie night with your mom?" Michelle asks.

"I don't know but I am gonna go to Luke's and pick up something to eat. I will call you when I'm am leaving and on my way home. Gets some sleep." Charlotte said hanging up.

She then turns back to her laptop goes back to work.

(Time Skip)

Charlotte was walking the streets of Stars Hollow heading for Luke's. She had finished working earlier and now she was starving. Her mom had come home earlier to change and head to the town meeting to deal with Taylor. Apparently she couldn't change anything about the Dragonfly Inn unless approved by the historical society.

Charlotte hadn't seen Rory after this morning and frankly she was kind of relieved. After the conversation with her mom last night, and the talk she had earlier this morning with Luke, Charlotte was feeling guilty about keeping the Jess situation a secret from her sister. Now she was dealing with her ex-boyfriend getting married. She was lucky her ex-boyfriend never lived in the same town as her.

Charlotte was soon in front of the diner. As she opened the door Luke was serving his last customer for the night. She went up to the counter and watched as Luke was wiping it down. Charlotte waited until he noticed her and he looked at her before walking in the back.

Ten minutes later he came back with a plate of burger and fries with a chocolate milkshake. He placed it in front of her with a small smile.

"Thanks Luke." She said as he continued cleaning up. As he was cleaning a group of boys drunkenly entered the diner singing.

"We do or die for Stars Hollow High! We do or die for Stars Hollow High! It's the one we fight and fall for, it's the one we give our all for." They sang off key.

Luke then sighed with annoyance at the groups singing. "Oh, Goody."

They then yelled "Stars Hollow High! WHOO!" The constant yelling was making Luke and Charlotte cringe. Charlotte looked at Luke and nodded her head to his apartment. He waved his hand to signal yes. She picked up her food and headed upstairs into Luke's apartment.

When she got upstairs the first thing she saw was Jess's bed. It made her realize she missed her friend and his standoffish ways. She sat down his bed and thought of the first time she met him.

 _(Flashback)_

 _Charlotte walked out of the school in a rush to get to the diner. She was working today and was really exhausted. It had been a week since Tristan left and Charlotte was angry. Angry at herself for letting things get this far with them. She just needed to put it in the back of her head._

 _As she walked into diner she saw her mom and Luke talking. She walked right passed them and headed to the back ignoring their presence. She put on her apron and walked out into the front and began taking orders. She then hears the bell on top of the door and a guy walks in. Charlotte has a look of annoyance on her face_

 _Jess walks into the diner and sees a girl his age taking orders. He can tell by the look of her face, that today is really not a good one. When he attempted to go straight upstairs his Uncle called his name._

 _"Jess, hey, good. I would like for you to meet someone." Luke said beckoning him over._

 _Jess walked up to the diner counter and saw a woman sitting there with a inviting smile. It unnerved Jess for some reason. He wasn't gonna let it show on his face though. The woman sitting waved her hand at him._

 _"Hey. Hi I'm Lorelai. I just wanted to meet you before Luke had a chance fill your head with all kinda lies about me." Lorelai said introducing herself._

 _"Hi." Jess stoically said._

 _"You know, you should meet my daughters. There both about your age. They can show you where all the good wildin goes on... Well ok it was nice to meet you. I hope you like living here... So, class dismissed." Lorelai awkwardly said to Jess._

 _Luke glanced up at Charlotte and saw her heading to the register. He knew she was hurting over Tristan leaving and while working was distracting her for the moment, Luke knew she was going to blow up soon._

 _"Hey Charlotte come here for a sec. I want to introduce you to Jess." Luke said_

 _Charlotte and Jess looked at each other and said "Hi". Jess then headed upstairs and Charlotte went back to work. As the teens went back to what they were doing Lorelai and Luke watched on sadly._

 _"So that's Jess?" Lorelai sarcastically asked._

 _"Yup." the diner owner replied looking at the spot where his nephew stood._

 _"Very chatty." Lorelai adds._

 _"He adjusting. He just got here. He probably just went out and realized there are twelve stores devoted to peddling porcelain unicorns. I"ve lived in this town my entire life, I still can't believe it." Luke reasons._

 _"I'm sure that's it." She said optimistically._

 _"He will be fine in a couple days" Luke adds._

 _Charlotte then walked over to them taking off her apron and handing it too Luke. He and Lorelai looked at her closely and saw she was exhausted._

 _"I finished taking all the orders and giving them their food. I'm not feeling too great today so I'm going home early if you don't mind." Charlotte told Luke who nodded at her. They watched her gather her things and walk out the diner quickly._

 _"When do you think she is going to let someone in and talk about it?" Luke asked Lorelai who was distraught in worry for her daughter._

 _"I don't know Luke. She gets angry whenever me and Rory bring his name up. When she is ready to talk I will always be ready to listen." Lorelai said._

 _"She's a good kid and she doesn't need all that." Luke said._

 _"On another note, I have a fabulous idea. what are you doing tomorrow?" Lorelai asked._

 _"Why?" He asked curious at what idea was running through her coffee muddled brain._

 _"Why don't you and Jess come over to dinner?_

 _"Dinner?"_

 _"Sookie will cook, Charlotte and Rory will be there. It'll be a little 'Hey, welcome to Stars Hollow and see, everyone here's not straight out of a Fellini film' kind of an evening"._

 _"Ok, that would be nice, thanks." Luke said appreciatively._

 _Luke walks away from Lorelai just as Rory walks into the diner._

 _(Time Skip)_

 _The next night Charlotte was in her room staring at drawing in her sketchpad. The drawing was of a dress she planned to make for a dance. It was supposed to be for her spring formal that Tristan was supposed to take her to. She picked the sketchpad up and threw it out the window._

 _Charlotte then heard a knock on her door. The door opened and her mom had entered and sat down on her bed._

 _"Hey sweets, Luke and Jess are going to be here soon. I want you to come downstairs soon." Lorelai said kissing her daughter's forehead before walking out of her room._

 _Charlotte sighs and begins to change out of her pajamas. She puts on a tight pair of blue jeans and olive green hoodie with a pair of brown heeled boots. Then Charlotte puts her hair in a ponytail and puts on some lipgloss on before heading downstairs. As she walks downstairs she hears voices in the kitchen._

 _Charlotte heads into the kitchen and sees Sookie and Jackson talking about the food they cooked. She glances into her sisters room and sees her working on the computer. Her mom comes from behind her and sees all the food._

 _"Oh, wow, something smells good" she praises to the cooks._

 _"It's the garlic." Sookie said._

 _"Three heads of it" Jackson adds._

 _"Nice" Lorelai praises once again._

 _Lorelai then turns to Rory's room and sees what she is doing on the computer. Charlotte turns around and goes outside on the back porch. She heads for the garage and sees her piano under a sheet. It was a gift from her dad when she was younger. In Charlotte's opinion it was the only nice thing her dad did for her._

 _She pulls the cover off of it and slides her hand across the keys. It gave her goosebumps thinking of all the lessons she went to. It helped her release all the emotions she felt as a child. Her mom told her the talent she had with her finger tips was amazing. She sat down on the bench and began to play something:_

 _This is a story that I have never told_  
 _I gotta get this off my chest to let it go_  
 _I need to take back the light inside you stole_  
 _You're a criminal_  
 _And you steal like you're a pro_

 _All the pain and the truth_  
 _I wear like a battle wound_  
 _So ashamed, so confused_  
 _I was broken and bruised_

 _Now I'm a warrior_  
 _Now I've got thicker skin_  
 _I'm a warrior_  
 _I'm stronger than I've ever been_  
 _And my armor, is made of steel, you can't get in_  
 _I'm a warrior_  
 _And you can never hurt me again_

 _Out of the ashes, I'm burning like a fire_  
 _You can save your apologies, you're nothing but a liar_  
 _I've got shame, I've got scars_  
 _That I will never show_  
 _I'm a survivor_  
 _In more ways than you know_

 _'Cause all the pain and the truth_  
 _I wear like a battle wound_  
 _So ashamed, so confused_  
 _I'm not broken or bruised_

 _'Cause now I'm a warrior_  
 _Now I've got thicker skin_  
 _I'm a warrior_  
 _I'm stronger than I've ever been_  
 _And my armor, is made of steel, you can't get in_  
 _I'm a warrior_  
 _And you can never hurt me_

 _There's a part of me I can't get back_  
 _A little girl grew up too fast_  
 _All it took was once, I'll never be the same_  
 _Now I'm taking back my life today_  
 _Nothing left that you can say_  
 _'Cause you were never gonna take the blame anyway_

 _Now I'm a warrior_  
 _I've got thicker skin_  
 _I'm a warrior_  
 _I'm stronger than I've ever been_  
 _And my armor, is made of steel, you can't get in_  
 _I'm a warrior_  
 _And you can never hurt me again_

 _No oh yeah yeah_  
 _You can never hurt me again_

 _Charlotte played the last note and took a breath and hear clapping behind her. She quickly turned around and saw the boy from the diner yesterday. Luke's nephew Jess, Charlotte thought. She stood up and tried to walk pass him only for him to grab her arm._

 _"Wait." he said making her turn around to look at him._

 _"What?"_

 _"You were good." he complimented._

 _"Thanks" she said._

 _"Where did you learn to play like that?" Jess asked._

 _"I took lessons when I was younger. It helped me release the negative emotions I felt whenever I played." She explained to him walking towards the porch and sitting down on the steps. Jess stood there awkwardly attempting to look cool before joining her._

 _"Well did it help you release anything this time?" He asked._

 _"Yeah." She said unemotionally making the boy take a closer look at her._

 _"who was the guy?"_

 _She turned to face him with a critical look. "What makes you think it was guy?" She asked._

 _"The emotion in your voice, the puffiness of your eyes, the tear streaks on your face. Take your pick" he said._

 _She made a sigh and explained to him all that had happened. Jess nodded at certain points of her tale before finally saying. "You don't need him. If he was dumb enough to lose you, then he wasn't worthy of your affection in the first place."_

 _Charlotte was shocked at what he said to her. He was right in the sense that he didn't deserve her. Here she was wallowing and being a moody bitch when a total stranger put things into perspective._

 _"Thanks Jess." Charlotte said softly getting up to go inside._

 _"It was nothing" he replied smirking at her._

 _"Are you coming inside?" she added._

 _"These type of things aren't my scene to be honest." He said noncommitedly._

 _"Well thanks for listening." she said going inside to eat. When she got inside the kitchen her mom was staring at her with a look of confusion._

 _"Is there something on my face?" Charlotte jokingly asked._

 _"You seem like yourself. How are you feeling?" Lorelai asked concerned._

 _"It still hurts but I can't let it dictate my life. Tristan was an idiot for not seeing what he had, His loss and someone else's gain. All it took was words from a complete stranger to make me see that". She said with small smile._

 _"Who was this complete stranger?"_

 _"Jess" Charlotte simply said heading for the living room leaving her mother to look out the back door window to see Jess leaning on the porch rail._

 _(Flashback Ends)_

Charlotte was broken out of her thoughts of Jess with Luke entering the apartment dragging a drunk Dean. She stood up from the bed as Luke held him so he wouldn't fall.

"Here we are" Luke said leading him closer to the bed.

"She's smart, man. You know, she's so smart" Dean said slurring his words.

"Who is he talking about?" Charlotte asked but Luke ignored her and made Dean more comfortable.

"I know, I know" Luke said to the boy.

"She could probably fix the world, you know?"

"Right, right. She could team up with Kyle – her brains, his brawn" Luke said.

"No not Kyle – Rory." He said getting a shocked reaction from Charlotte.

Had she not have been there Charlotte would not believe the words that had come out of his mouth. In the back of her mind Charlotte knew on some level Dean still wanted to be with Rory. This just made things all the more complicated. She was so glad she said no to Lindsay.

"Almost there." Luke said placing him on the bed.

"She's the one, you know." Dean said still rambling in his drunken haze.

"Dean stop talking and lay down right here" Luke said taking Dean's shoes off to make him more comfortable.

"I miss her. Why didn't she love me?" Dean said the last part softly as he passed out.

Luke turned around too see Charlotte glaring at Dean. He knew this was going to be bad, especially with they way Charlotte has been team Jess lately. He turned off the lights and led her down the stairs back into the diner. When they got downstairs Luke turned Charlotte to face him.

"I know you have something to say now spit it out."

"Do not tell Rory what Dean said." She said to Luke.

"I wasn't going to tell her. I am going to tell her not to go to the wedding. She and your mom were invited by Dean himself." Luke explained.

"Do it subtlety so Rory doesn't get suspicious. After the whole Jess thing, Rory needs to focus on herself at this moment and Dean will ruin that. I love my sister but when it comes to the guys she's dated she is ruled by her emotions. For the first time since Dean moved to Stars Hollow, Rory is single and happy and I want for her to be this way." Charlotte said with a look of seriousness.

"I understand Charlotte" He said pulling her into a hug and kissing her forehead. "Your a good sister, you know that?" He adds.

"Rory would do the same for me. I think" she said just as the diner door opens to reveal Lorelai. She walked further into the diner and stopped in front of Luke and Charlotte.

"What are you talking about?' She asked.

"Nothing mom," Charlotte said before turning to Luke. "Thanks for listening Luke earlier im gonna go home and pack so i can leave tomorrow morning. Charlotte gathered her things and waved on last time before walking out of the diner.

(Time Skip)

With the last of her things packed Charlotte headed downstairs and saw her mom and Rory sitting on the couch laughing at whatever was on the screen. She went towards the kitchen and headed for the back door. She headed for the garage and saw her piano sitting there. Someone had cleaned it recently. As Charlotte sat down she heard a sound and turned to see her mom.

"The last time I can remember you playing this was the night Jess came over for dinner. The one nice thing I could say about him is he knew how to get you to open up when I couldn't." Lorelai states sitting next to her daughter.

"He is a good friend to me. Hell I consider him a brother more than a friend." Charlotte said to her mother.

"You were right about what you said last night. I never tried to give Jess a chance. After he was rude to me that night and he started dating Rory. I wasn't receptive because I thought Dean was the better choice." Lorelai explained her reasons.

Charlotte turned to her mother and grabbed her hands. "Mom I get it Dean was the boy next door. The boy you bring home to meet your mother, while Jess is a nightmare waiting to happen. But you have to give Rory credit where its due and you can't blame Jess for everything. It takes two people to make a relationship work, and I have faith Jess will come back and he and Rory will fix or salvage whatever's between them." Charlotte said making her mother nod in agreement.

"I know, I just worry about you guys when it comes to dating. I dont have the greatest dating life and I don't want that affecting yours." Lorelai said.

"I get that. I really do, but you have to give us room to make our choices without feeling like you disapprove. Unless you would rather I treat you like Emily." Charlotte said placing her hands on the keyboard.

"God No! Please don't ever compare me to my mother. So what are you about to play sweets?"

"Something comes to mind" Charlotte said

 _Step one, you say we need to talk_  
 _He walks, you say sit down, it's just a talk_  
 _He smiles politely back at you_  
 _You stare politely right on through_  
 _Some sort of window to your right_  
 _As he goes left, and you stay right_  
 _Between the lines of fear and blame_  
 _You begin to wonder why you came_

 _Where did I go wrong?_  
 _I lost a friend_  
 _Somewhere along in the bitterness_  
 _And I would have stayed up with you all night_  
 _Had I known how to save a life_

 _Let him know that you know best_  
 _Cause after all, you do know best_  
 _Try to slip past his defense_  
 _Without granting innocence_  
 _Lay down a list of what is wrong_  
 _The things you've told him all along_  
 _And pray to God he hears you_  
 _And I pray to God he hears you_

 _Where did I go wrong?_  
 _I lost a friend_  
 _Somewhere along in the bitterness_  
 _And I would have stayed up with you all night_  
 _Had I known how to save a life_

 _As he begins to raise his voice_  
 _You lower yours and grant him one last choice_  
 _Drive until you lose the road_  
 _Or break with the ones you've followed_  
 _He will do one of two things_  
 _He will admit to everything_  
 _Or he'll say he's just not the same_  
 _And you'll begin to wonder why you came_

 _Where did I go wrong?_  
 _I lost a friend_  
 _Somewhere along in the bitterness_  
 _And I would have stayed up with you all night_  
 _Had I known how to save a life_

 _Where did I go wrong?_  
 _I lost a friend_  
 _Somewhere along in the bitterness_  
 _And I would have stayed up with you all night_  
 _Had I known how to save a life_

 _How to save a life_  
 _How to save a life_

 _Where did I go wrong?_  
 _I lost a friend_  
 _Somewhere along in the bitterness_  
 _And I would have stayed up with you all night_  
 _Had I known how to save a life_

 _Where did I go wrong?_  
 _I lost a friend_  
 _Somewhere along in the bitterness_  
 _And I would have stayed up with you all night_  
 _Had I known how to save a life_

 _How to save a life_  
 _How to save a life_

As the last key played Lorelai looked at her daughter and saw she was tired. She hugged her daughter close and kissed her on the forehead. "I know how much Jess means to you sweets. So I will try to be open to getting along with him for you and Rory's sake the next time he is around."

"That's all I ask mom. Now let's go to bed cause i have to drive back to the city tomorrow morning." she said getting up to go inside. Lorelai put her arm around her daughter's waist and they both headed inside.

(Time Skip)

Charlotte had just finished putting her stuff in the car. She had said her goodbyes to her mom and Rory last night before going to bed. Her mom had left earlier to go meet up with Sookie and Michel to talk about the Dragonfly Inn. Rory had woken up before both of them and left the house in a rush.

Charlotte got in the car and quickly drove into town. As she was passing through town she saw Dean and Lindsay exiting the church. Lindsay noticed the car and waved towards Charlotte as she drove pass the newlyweds. Charlotte waved back at her and continued driving until she was in front of the diner.

She got out of the car and headed inside to see Luke yelling at Taylor to get out once again. Charlotte then sat down at the counter next to Rory who hadn't noticed her. She tapped her sister on the shoulder making her turn to see Rory try to fake a smile.

"Don't you give me that fake smile Rory." Charlotte told her sister as Luke put a cup of coffee and a banana nut muffin in front of her.

"He could of done more with his life instead of marrying so young." Rory replied

"Well that is his mistake to make Rory. You can't make someone want more for themselves if their not even trying. You tried this with Jess and sad to say he wasn't ready. Now your trying that with Dean. Neither one of them need judgment cast towards them so if you want them in your life keep your opinions to yourself." Charlotte advised.

Rory nodded at her sister's words but Charlotte knew everything she said just went in one ear and out the other. She knew for Rory to understand what she said she would have to learn the hard way. Charlotte hoped Rory didn't do anything stupid cause she wasn't gonna be around to lean up and fix like she normally does.

Charlotte finished her food and gave Rory a nudge. Rory turned to her sister and saw she was finished eating.

"You leaving now?" Rory asked.

"Yeah I got class and work tomorrow. I have a very hectic schedule for the next couple of weeks. I probably won't be coming home for our birthday." Charlotte said.

Rory got up from her stool and hugged her sister. "Call me, Charlotte."

Charlotte was heading for the diner door but a hand stopped her. She turned to see Luke giving her a look. She gave him a hug and he nodded at her. Charlotte got in the car and looked around and saw the beauty of Stars Hollow. It made her kind of sad to leave but in the end she would be back. She started the car and drove off heading home. To the where the drama is going to begin.

*The next chapter will be titled "Daddy Dearest" and the drama between Charlottte and her father will unfold.

*Jess will be appearing next chapter and he is going through it and who better to help him then Charlotte.

*Charlotte wont be making any decisions about her love life anytime soon but here there Austin and Tristan will fight over her.

*The song(s) are as follow

 _"Warrior" by Demi Lovato_

 _"How To Save A Life" by The Fray_

Chaz746


	9. Daddy Dearest

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS**

The Life & Times of Charlotte Gilmore Chapter 8: Daddy Dearest

After the long weekend Charlotte had she was ready to catch up with her friends. So they had all decided to meet up and have breakfast at a small café downtown near Battery Park. The four friends were waiting on their meals as Charlotte regaled them about her weekend.

"So let me get this straight Dean still wants to be with Rory but he married Lindsay?" Michelle asked.

"He said the words in front of me and Luke. If I wasn't there myself guys I don't know if I would have believed it either." Charlotte said.

"It must be kinda awkward that you know he said this and you have to act like nothings happened." Ethan awkwardly said.

"You have no idea." Charlotte added.

"Did you tell your sister? Sienna asked

"No and to be honest I don't want to. Rory is finally in a good place and I don't want to be the one to ruin her happiness. I'm not gonna let Dean hurt my sister and make her feel less than what she is." Charlotte explained as the waiter came with their orders.

"Enough with the Stars Hollow drama, Charlotte. What are you gonna do about Austin and Tristan?" Michelle asked her best friend.

"Well after speaking with my mom I realized that I'm going to take it slow with Tristan and get to know Austin before I just jump into a relationship. I figured since I'm not in a relationship I could just hang out with both of them." She said eating her salad.

"Hopefully it doesn't blow up in your face." Ethan added drinking his lemonade.

"What do you mean by that Ethan?" Sienna asked.

"Well if I was seeing a girl and found out she is talking to another guy besides me I would be pissed. I would rather the girl be upfront with me then talking to someone behind my back. That's just me, and from what you told us Tristan wants more from you than friendship. So if I were you I would tell him about Austin." Ethan explained to the girls making them all look at Charlotte.

"I just don't want to be in the middle of this." Charlotte grunted.

"Too late." Sienna said making the table laugh at Charlotte's life.

"Did you finish your proposal for Harper? Do you want my help with the finishing touches?" Sienna asked.

"Everything is practically done. All I have to do is show it to Harper and see what he thinks." Charlotte said looking at her watch.

"Are you late for something?" Ethan asked as the group were eating their food.

"Yeah I'm going to meet Jess so we can talk. I feel like I should tell him what happened but then again I don't. Its confusing to say the least." Charlotte tells her friends.

"I don't think you should tell him at all. Jess blew every chance he had with Rory and its not fair to her for him to keeping popping in and out of her life. He needs to work out his personal issues before he puts himself into a relationship." Michelle said.

"I have faith in him and maybe they will eventually get together. I don't see Rory and Dean ever getting back together. Now I will see you guys later." Charlotte said getting up from the table and walking away from her friends.

(Time Skip)

Charlotte had just got off the train and saw Jess waiting for her on the platform with a grin. She walked up and hugged him.

"Come on lets go to my place." He said pulling her arm as they walked out of the subway station. They got up to the street level and started walking.

"What have you been up to Mariano?" She asked curious about her friends life.

"Don't laugh at what I am about to tell you. I got my G.E.D. a couple weeks ago and I started taking college classes over at BMCC. I've been taking a couple of literature and writing classes." Jess said.

"Why would I laugh at that? I am proud of you for finally wanting more for yourself. You look happier since I last saw you." Charlotte said smiling at her friend.

"After our last conversation I realized I wont truly be happy unless I want to. So the reason I am going back to school is I am writing a book." Jess plainly stated waiting for a typical Gilmore reaction.

"Ok" She said.

Jess gave her one of his "You're Cracked" looks. "Just Ok, nothing else to add?" He asked.

"I'm not going to pry until the product is finished. I believe you will write a masterpiece and I will wait. So until then keep writing Ernest." Charlotte said amazing Jess.

"You have a lot of faith in me."

"In my eyes Jess, no matter what I've got your back. Even if others look at me crazy I will be in your corner." Charlotte said.

"Enough about me, What's going on in your life?" Jess asked.

"Well not to brag or anything but school and work are going great for me." she said as they walked into a building

"What about you personally Charlotte?" He asked as they walked up a set of stairs

"Tristan is back in my life. Michelle and I ran into him when we went out to dinner a couple weeks ago. Then I had lunch with him last week. I don't know how I want him in my life. Then on top of that my neighbor asked me out when I went to his party. So I'm trying to figure things out." Charlotte explained rambling.

"Just take it day by day. Don't rush into anything" Jess advised as they got to his apartment door.

When he opened the door Charlotte saw that Jess's apartment was a mess. His mattress was on the floor, trash was thrown around the room, and clothes were lying all over the floor. Charlotte was getting more worried about her friend and his living situation.

"Wow Holden Caulfield much?" Charlotte jokingly asked.

"I know this place is crap and all but its what I can afford." Jess said looking around his apartment. He headed into his kitchen and started opening cabinets and pulled out a bowl and spoon. Jess then opened his fridge looking for something

"I'm thinking of having a movie night at my place. Order everything the city has to offer and just hang out. You are more than welcome to come."

"Whose going to be there?" Jess asked while he is looking in his fridge.

"Well I am inviting my friends Ethan, Sienna, and maybe Tristan. Michelle is probably going to invite this guy she met at Austin's party. If you feel up to it that is." She said.

"I'll let you know if I am not working." He said closing the fridge door with an ice cream bucket in his hand

"Well on that note I have to get ready for work so I will call you later" She said walking towards the door.

"How is Rory doing? Jess asked silently just as her hand touched the door. Charlotte turned her head to look back at him.

"Are you sure you want to know?" Charlotte hesitantly asked Jess whose face showed nothing.

"I still care about her. Even though I don't know how to show it properly I care about her."

"Rory is fine, Jess. If you really want to knowhow she is really doing, go and ask her yourself. Charlotte said opening the door and walking out of Jess's apartment leaving him alone once again with his thoughts and regrets.

(Time Skip)

Charlotte was sitting at her desk at work going over her conversation with Jess. She was happy that he was getting his life in order. She was worried about his living situation which really bothered her. When he asked about Rory it made her conflicted because she wanted Jess to fix it on his own.

Sienna walked into the office and went up to Charlotte's desk. She tapped the desk to get her friends attention. "Ursula wants to see us in her office right now."

Charlotte nodded and gathered her notepad and followed Sienna to Ursula's office. They walked down the hallway and passed by other employees rushing to do their jobs. Sienna knocked on Ursula's door when they stood in front of it.

"Come in" Ursula's voices answered.

Sienna opened the door to Ursula's office and saw Ursula sitting in her chair behind her desk. In front of her desk sitting was Rafael, Harper, and Yolanda. Sienna entered the room with Charlotte closing the door behind her as she followed into her office.

"Now that the interns I have good new to tell you about the venue. You will not have to search for a venue anymore. I have recently spoken to the staff at the Waldorf Astoria and I have procured a deal to have the hotel be the prime place for the Gala event." Ursula explained to them.

"That is great Ursula. So what do you want to do first?" Rafael asked.

"I want some photos taken of the ballroom so we can decide how to setup for everything. I want the plans for everything on my desk by this Friday."

"I will send Yolanda and the girls to get that done. Anything else we should know about?" Rafael responded.

"Yes, as a matter of fact there is? How is the planning for the expo at FIT going Ms. Gilmore? Ursula asked curious at what the girl had come up with.

"I was going to meet with Harper in his office and go over the last minute ideas with him." Charlotte said.

"Well since we are all here why don't you explain to us what you have here. Unless you have nothing to prepare." Ursula said curtly making Charlotte nervous.

"I thought that we could hold the expo in one of the museums in the school. You and two other judges would pick the designers that you would deem fit for the gala event. Since you already have fifteen upcoming designers all you need is ten more. Like I said at the meeting you would speak with the school to hold the event."

"I want this idea implemented on Friday as well. Now I have to go to the Waldorf Astoria and I would like for Yolanda and the girls to come with me. After we get the photos done and see the layout of the hotel you girls are going to meet me in the dining area and meet a friend of mine." Ursula said getting up from her chair.

"Ursula wasn't there something else you had to say?" Harper asked making her sigh in annoyance.

"Oh yes there was. Girls tomorrow one of my important clients will be here for a fitting for a dress and I need for both of you to be here." Ursula explained dryly.

"Who is the client?" Sienna asked while Charlotte was taking notes on everything that had been spoken.

"Sarah Jessica Parker" Harper said calmly.

Charlotte was excited to meet Sarah Jessica Parker. The woman had great fashion sense and she loved her on _Sex and the City._ To think that they would be in the same rom as her was amazing to say the least. Hopefully she won't embarrass herself in front of the woman.

"Since that has been dealt with let us go to the hotel." Ursula said walking out of her office with everyone following right behind her.

(Time Skip)

Charlotte was taking photos of the grand ball room to get an idea of how they were going to setup everything. Sienna was sketching a floor plan of how things were going to look. Yolanda was talking to one of the coordinators for the hotel.

"Char can you come over here for a second" Sienna called.

Charlotte walked over to her friend and saw her staring intensely over at her floor plan.

"What's up?"

"So I was thinking we place a runway in the middle of the ball room so the models can walk with the designers work. Then we put tables surrounding the walkway so the guests can see the work. What do you think?" Sienna asked.

Charlotte looked over the floor plan and saw how the layout would look. In her opinion it was perfect all they needed was to run it by Yolanda.

"Seems fine to me. Ask Yolanda what she thinks and if she likes it show Ursula." Charlotte turning to walk away.

"Charlotte what were you thinking about back at the office earlier? You've been a little distracted since you saw Jess. What happened when you met up with him?" Sienna asked concerned.

Charlotte sighed before sitting down next to Sienna. She told her what they had talked about and Sienna could see the strain on her friends face from talking about him was causing.

"At least he is attempting to get his life in order. That's more than most guys with his type of background." Sienna said once Charlotte finished.

"You're right about him trying to fix his life. I just want my friend to be happy even if he and my sister never get back together. All I want is for him to fix the mistakes and problems he caused. Is that so bad?"

Sienna stopped what she was doing to give her full attention to her friend. The thing she liked the most about Charlotte was how optimistic she was about someone. She really cared about Jess even with all his personal struggles when no one else believed in him. Charlotte was a real loyal friend even when the person sometimes didn't deserve it.

"From what you told me about Jess it seems like he knows he messed up. It's just that he needs to figure out how to fix on his own," When Sienna saw Charlotte begin to frown she continued. "Not that he doesn't appreciate your help, Charlotte. Jess for his own personal reasons need to do this himself and you as his friend should allow him to do that until he asks you for help. The first step is seeing all the problems he caused and going from what you said he still has feelings for Rory. When he is ready he will know what to say."

"I know, I just have this need to make things go back to what they were." Charlotte said.

"Life is all about change and sometimes we have to embrace it even though we're not ready for it. You of all people should know about change especially with Tristan back in your life." Sienna reminded her friend who blushed.

At that moment Yolanda walked over to them and saw the floor plan Sienna had drawn up. "Wow Sienna this is a pretty good floor plan and with the photos Charlotte has taken I think we can get everything planned and set up with in the next two weeks. Now I just got off the phone with Ursula and she is waiting for us in the dining hall with Harper and an old friend.

Charlotte and Sienna began to pack up their materials for the gala event and then followed Yolanda out of the ballroom. Eventually they reached the dining hall and saw the maître d' of the dining hall.

"Welcome to the Waldorf Astoria is this your entire party or are you meeting someone?" He asked.

"Ursula Underwood is waiting for us in the private section." Yolanda simply said.

"Follow me please" he requested as he led them pass other clientele until they reached the back of the dining hall. They saw Ursula and Harper eating with a young man and an older woman whose back was to them. From what Charlotte could see about the two people, The woman was in an eggshell colored business suit with her hair in a tight bun, The man was in a charcoal gray suit his hair was over gelled in Charlotte's opinion.

When they reached the table and saw the people sitting with their boss Charlotte stiffened. It was noticed by Sienna and she saw her friend's face become emotionless. She had never seen Charlotte's whole attitude shift so quickly and it worried her.

"Char you ok?" She asked in a whisper.

"I will tell you everything after this. For now I am fine." Charlotte said cryptically making Sienna nervous.

While the girls were talking quietly Yolanda was informing Ursula and Harper on all the planning that happened in the ballroom. "I have to say I am impressed with the girls teamwork on this project. Sienna came up with a way to present the designers work by building a runway in the middle of the ballroom with several small tables surrounding it. Charlotte took photos and measurements of the room so we can have the spec ready." Yolanda informed.

"I can't wait for everything to be executed and I need to see the presentation Charlotte has for the student showcase at FIT. Otherwise the gala will fall apart but just in case I need you to find backup designers." Ursula said getting slight nods from Yolanda and Harper.

Ursula stood and placed her hands on the girls shoulders and brought them closer to the table. "Francine I would like for you to meet my interns Sienna Miller and Charlotte Gilmore," She then motioned the girls to sit across from Francine and the young man. "Girls I would like for you to meet Francine Hayden and her son Christopher. Francine and I were sorority sisters in our heyday. We have been friends for over 39 years and she will be hosting the gala for me." Ursula said smiling as she sat down.

When Charlotte's name came out of Ursula's mouth, Charlotte saw Francine face drop and Christopher smile.

"Charlotte I didn't know you worked for Ursula. What are you doing here in New York?" Christopher asked.

"In order for you to know what I am doing you would have to actually call me." Charlotte said taking a sip of her water.

When Charlotte said that Christopher's smile disappeared and he cleared his throat. "I know I havent always been there Charlotte but you never let me in. You never gave me a chance like Rory, she at least hears me out." Christopher said making his daughter glare at him.

"I never gave you a chance! If anything I was the one who convinced Mom to try and make it work when we were younger. Only, once again you ruined any chance you had with Mom. You don't know when to grow up and own up to your mistakes." Charlotte exclaimed with rage.

"What are you talking about? I always wanted to be with your mom and you girls." Christopher said.

"Ugh! You don't get it. Every time you came into our lives you gave me and my sister false hope that we were going be a family. Then I truly saw who you were. A flake. Then you go and get that woman pregnant and have a whole new family, forgetting the one you have."

"Charlotte I am still you dad at the end of the day. No matter how angry you are with me I will always love you" He said with a smile until it vanished from his face at Charlotte next words.

"You are not my dad Luke is. He was there for every important moment in my life. He was the one who taught me to drive. He was the one who took me to my father daughter dance because you were too busy with whatever the hell you were doing. So you are not my dad. A dad is always someone who I can count on, and right now I don't want you in my life at all. So go be a dad to your new daughter."

"Charlotte you don't mean that."

"You are nothing but a sperm donor to me. From now on you have two daughters and I am ok with that." She said feeling so much better getting that off her chest.

Everyone at the table was feeling uncomfortable at Charlotte and Christopher's conversation. They could hear the animosity coming out of Charlotte's lips as she spoke to Christopher and they were all confused.

"Charlotte what is the meaning of this?" Ursula asked her intern with curiosity.

"Where are my manners?", Charlotte stood from her seat and made a waving motion to Christopher. "Ursula I would like for you to meet my father, Christopher Hayden." She said making Francine look around the dining hall at the other clientele who were attempting to not watch the commotion.

"Young lady sit down right now! You are embarrassing us with your theatrics." Francine scolded Charlotte who rolled her eyes.

"Well I at least acknowledge who you are Francine. A hypocritical bitch who blames my mother for how much of a fuck up her son is. It takes two to make a baby remember that." She said making Francine look at her with shock. Christopher on the other hand looked at his daughter and saw all the anger in her eyes. He had caused that and Lorelai warned him, now it was too late to have any part in her life.

Charlotte gathered her things and turned to Ursula. " I am so sorry for what has happened tonight and I hope this doesn't make you think differently of me. Hopefully this doesn't affect my future being your intern cause I really like working for you." Charlotte said walking out of the dining hall in a quick pace.

When Charlotte walked out of the hotel there were tears all on her face. She was emotionally drained from being around Christopher and she was so over tonight. Everything she had felt had lashed out tonight and she was embarrassed from doing that in front of her boss.

Charlotte needed to get away from her so she pulled out her phone. She then scrolled through her contacts and pressed call on Tristan

"Hey Char, what's up?" Tristan said picking up immediately.

"Can you come and pick me up at the Waldorf Astoria. I need to get out of here right now and you were the only one I wanted to call." She said sniffling

"What happened? You sound like you are crying" He asked with care in his voice.

"I will tell you as soon as you get here." She said frantically.

"Ok I will be there in fifteen minutes I'm in Brooklyn." He said.

"Thanks Tris" Charlotte said hanging up an putting her phone in purse.

Charlotte sat down on the curb looking at the skyline of the city. Almost every time she looked up, Charlotte was reminded that she came to New York to get away from the views of Hartford Society. Today she learned a lesson that she will never forget. Your past is always with you no matter how far from it you are.

"Charlotte there you are. I've been looking for you all over the hotel" Sienna said running to her friend. Sienna sat down on the curb next to her and hugged her friend tight.

"Are you ok?" Sienna asked as they broke the hug.

"No not really, I need to get out of here. When I am around him all I see is the pain he caused Rory, my mom and I. The worst part is I let my emotions take over. I embarrassed myself in front of all those people in that room. What happened after I left?" Charlotte said wiping her tears from her face with her sleeve from her blouse.

"Well after your grand exit, Ursula cut the meeting short and left with Harper and Yolanda. Before she left she wanted me to tell you she still expects her presentation." Sienna informed her friend.

"How are you getting home?" Charlotte asked.

"I was thinking about taking a cab." Sienna said.

"I was going to ask you before all the drama if you wanted to sleep over tonight. Unless you have plans with Ethan tonight?"

"Actually I told him to meet me at your place so we can all hang out in your apartment tonight. I figured you didn't want to be alone." Sienna said.

"Well in that case you are catching a ride with me and Tristan." Charlotte said just as a black SUV pulled up in front of them.

As the car stopped Tristan got out of the driver's side and walked up to them. He was wearing a leather jacket over a white shirt, with a pair of dark blue jeans and boots. He smiled as he got closer to her pulling her into his arms.

"You sounded upset over the phone. Care to tell me what happened." He asked cautiously.

"First I would like for you to meet my friend Sienna," She then turned to Sienna. "Sienna I would like for you to meet Tristan". Charlotte said introducing them.

"Hi" Sienna said as Tristan waved to her in return.

"Thanks for coming." Charlotte said making Tristan give her a small smile.

"Like I said before I heard you crying on the phone. I rushed over here as fast as I could. What happened tonight that made you like this?" He asked concerned.

"I will tell you on the way to my apartment. I just need to get away from here before I get mad all over again. Sienna is coming with me, I hope that is ok with you?"

"It's fine Char, I'm worried about you though." He said opening the passenger door for her.

Charlotte got in the car and closed her door making Tristan and Sienna talked outside. She couldn't hear what they were saying. Every few moments Tristan would look her way so she rolled the other way. Eventually they both got in the car and Tristan put his right hand in her left hand giving it a squeeze. Charlotte looked as Tristan once more before closing her eyes falling asleep.

(Time Skip)

Charlotte felt someone shaking her on her right shoulder. She opened her eyes and saw Tristan holding the car door open for her.

"How long was I asleep?" Charlotte asked.

"You fell asleep for thirty minutes. Sienna gave me your address and on the way I picked up pizza, which Sienna brought upstairs. There was a little traffic but we got her in one piece" he explained helping her out of the car.

They both walked inside the lobby and saw Mr. Jones behind the front desk. He noticed them and waved them over.

"Miss Gilmore you received a package that came an hour ago." Mr. Jones said handing her a box with a card on top of it. Charlotte took the package from him and thanked him. She then led Tristan to the elevator and the doors opened. They both stepped on the elevator and she pressed the number six.

"You didn't tell me what happened tonight. I haven't seen you like that since the day your dad came back into your life," He said noticing her flinch. "Is that what happened?"

When Charlotte nodded he immediately pulled her into her arms. He felt her shake in his arms and his shirt became damp.

"I tried so hard to become numb when he is around, but my emotions come out and I lash out. He never gets why I am angry and all I see is red. I'm tired of feeling like I am an on a rollercoaster Tristan" she said sniffling.

"Charlotte you can't blame yourself for how you feel. If anything you need to stop bottling up how you feel about him. Have you told your mom what happened tonight?

"No, you were the first one I called." She said making him happy at the thought that he was the one she called in his time of need.

The elevators door opened on the sixth floor and Austin was standing there. He had a smile on his face until he saw Charlotte's. From what he could tell it had looked like she was crying. He then noticed a guy standing next to her and he was holding her in his arms. To say he was jealous would be an understatement.

"Charlotte are you ok?" Austin asked.

Charlotte pulled away from Tristan and nodded at Austin. She stepped off the elevator and walked passed him. When Tristan tried to follow her Austin blocked him. "What happened to her tonight?" Austin asked watching her open her apartment door and closing the door softly.

"Look dude I don't even know you. If you really want to know you should ask Charlotte. Come on follow me." Tristan said leading Austin into Charlotte's apartment. When they walked in they saw Michelle, Ethan and Sienna sitting in the living room staring at Charlotte's bedroom door.

"Why are you all staring at her door?" Tristan said.

"We haven't heard a sound since she came in ten minutes." Michelle explained worried about her best friend.

"Well right now she needs us to be there for her. One of us should call Lorelai to speak to her. She is emotionally exhausted right now and Lorelai is the only one to get her to open up." Tristan said.

Michelle pulled at her phone and dialed Lorelai who answered on the first ring.

"Hey Michelle how are you doing? Lorelai answered.

"I am fine Lorelai but there is a reason I called you. Charlotte had a bad day today and I was wondering if you can come to our apartment tomorrow."

"What happened?"

"She ran into Christopher while she was at work and it got really nasty. Tristan brought her home and now she is in her room and we don't hear a sound. We are worried about her and we don't know what to do." Michelle said.

"Don't worry Michelle I am on my way with the cavalry. Sit tight and I will call you when I am there." Lorelai said hanging up the phone.

They all looked at each other and began to wait for Lorelai to call.

(Time Skip)

After waiting for an hour and twenty minutes Lorelai called and said she was downstairs. Michelle gave her directions to the apartment and soon they heard a knock at the door. Michelle opened the door and saw Lorelai standing on the other side with Rory and several bags that said Luke's. She led them inside and Lorelai noticed several people in the living room.

"Who are all these people?" Lorelai asked with confusion.

"Charlotte hasn't told you about who she hangs with? I thought she told you what has been going on when she visited over the weekend."

"She did but I am trying to put names to faces." Lorelai said.

"You already know Tristan, sitting next to him are Sienna and Ethan, lastly on the other chair is Austin." Michelle said just as they heard Charlotte's door unlock. Charlotte had changed into her pajamas and she headed into the kitchen ignoring everyone.

Lorelai put down her stuff and tapped her daughter on her shoulder. Charlotte turned towards her mom and sighed. "Hi Mom." She said softly.

"Hi sweets. I heard you had a trying day so I brought comfort food and a Gilmore deluxe movie session. Why don't Rory and I set everything up while you finish up in here." Lorelai offered as she hugged Charlotte.

"Do whatever you want Mom I just want to go to sleep. I just want to unwind tomorrow we can talk about it." She said taking her food into her room.

As her bedroom door closed Charlotte looked at the package she received earlier. She walked over to it and saw the card that was attached. Charlotte tore it opened and saw it was from Christopher.

 _Dear Charlotte,_

 _Seeing you earlier tonight made me realize how much I missed in your life. You've grown into a beautiful intelligent woman and I had nothing to do with it. I have a lot of regrets in life but you and your sister are my greatest treasures. Just know that I wish you all the best in all you do. I hope you like what's inside the box._

 _Love Dad_

Charlotte put the card down and opened the box. Inside the box was a photo album. She opened the box and saw pictures of herself and Rory growing up. What really caught her eye was the recent photos like her high school graduation pictures, prom pictures and her softball championship photo with her holding a trophy.

"Where did he get these?" Charlotte said to herself.

"From me," Rory said getting her sisters attention. "Whenever I would speak to him he would always ask how you were doing. Since I know you guys weren't speaking I would send him photos of everything we did. It was a way for him to feel like he was part of our lives." Rory reasoned when she saw her sister getting angry.

"Rory I know you are trying to help but you had no right. You of all people should know how I feel. He has made promises to us over the years and then broke them. The reason I don't want him around me is because I don't trust him. His words mean nothing to me, so for future references keep me out of your conversations. I am done with him and it is going to stay that way." Charlotte bitterly explained.

Rory saw the rage on Charlotte's face slowly disappear. She really hoped her mom knew what to do about Charlotte's daddy issues otherwise their might be an encore later down the line.

*The next chapter will be up sometime in late April and it will be titled "Big Girls Don't Cry"

PLEASE GIVE YOUR OPINION AND LEAVE A REVIEW

CHAZ746


	10. Big Girls Don't Cry

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS** **.**

The Life & Times of Charlotte Gilmore Chapter 9: Big Girls Don't Cry

Charlotte felt the sun shining on her face. She rolled over and saw her sister sleeping right beside her. She then remembered all that had occurred the night before. Charlotte was mad at herself for allowing Christopher to get to her. She saw the box from him on the side of her bed. Looking at it brought the feelings from last night back.

Charlotte got out of her bed and opened her bedroom door. What she saw in her living room tugged at her heartstrings. All of friends were sleeping on the couch in very uncomfortable positions. On the sofa Ethan and Sienna were snuggled up with one another. Austin was on the floor snoring, which made Charlotte silently laugh. Charlotte glanced at Tristan who was awake and staring at her lovingly.

"How long have you been awake?" She asked.

"I woke up as soon as you opened your door. How are you feeling?" Tristan said getting up from the couch to stretch.

"Numb." Charlotte said.

"What's the plan for today?"

"At the moment I want to reassure my mom and Rory so they can leave. Then I want to go to work so I can apologize to Ursula for embarrassing her." Charlotte said heading into the kitchen.

Tristan follows her into the kitchen and watches her make breakfast. He sits down at the kitchen table and continues to watch her. He could tell she was still emotionally drained from yesterday. Charlotte was cracking several eggs into a bowl and began whisking them. She glanced behind herself to see Tristan lost in thought.

"Penny for your thoughts?" She asked catching his attention.

"I'm just worried about you."

Charlotte put the bowl of eggs down on the counter and walked over to Tristan. She put her arms around his neck. He looked up at her and smiled softly at her. She kissed his forehead and sat down in his lap.

"There are going to be days where I can't handle things."

"I know I just don't want you to close people off. When you do that it makes them worry even more. Its ok to let things go once in a while." Tristan said gaining a quizzical look from Charlotte.

She stood up from his lap and sighed. "Maybe I have let things fester too long. It just hurts to think about it because it brings up all the bad memories. I just wish he tried harder to be involved with me and Rory."

Tristan glanced over to Michelle's room and saw Lorelai standing there. She had probably heard their entire conversation.

"Charlotte why havent you said this before?" Lorelai asked surprising her daughter.

Charlotte quickly turned around saw her mom standing behind her.

"Mom, how long have you been standing there?"

"Long enough to know my daughter has a serious daddy issues. I know I let things with your dad slide a lot in the past, but you and your sister are always going to be my top priority." Lorelai said.

"I know Mom and I get that. I just need to figure out a way for me to let out all this aggression without letting it negatively affect my life." Charlotte said before turning to Tristan. "Do you mind finishing breakfast while I get ready for work?"

"No go right ahead. Everything will be done by the time your ready." He said watching her go into her bedroom.

When Charlotte closed her door Tristan picked up the bowl of eggs that Charlotte had beaten and continued making breakfast. Lorelai sat down in the chair Tristan was sitting in and watched him. As he was cooking Lorelai thought about the words Tristan spoke earlier to Charlotte. She realized he still loved her daughter and if anything it made her happy.

"You still love her don't you?" Lorelai asked Tristan out of the blue. He stopped what he was doing to give her his full attention.

"I never stopped loving her. Meeting your daughter in that restaurant is my second chance with her and I am not messing that up."

"She told me about that but she also told me something."

"What?"

Lorelai looks over into the living room and sees Austin still sleeping. "You might have some competition when it comes to Charlotte." She said getting a perplexed look from Tristan.

"With him?" Tristan mockingly said while glancing at Austin

"Just know that I am rooting for you." Lorelai said giving Tristan more to wonder about the future of his relationship with Charlotte.

(Time Skip)

When Charlotte came out of her bathroom fully dressed she saw Rory wasn't in her bed. She headed out into the living room and saw Rory, Michelle, Sienna and her mom laughing. She quickly glanced into the kitchen and saw the guys putting all the food on the table. She sat down next to Rory who glanced at her with a small smile.

"Did you sleep alright last night?" Charlotte asked.

"Yeah, your bed is pretty comfortable. Are you feeling better from last night?" Rory asked in return.

"I will be but if everyone keeps asking I will have a psychotic breakdown and then I won't" Charlotte sarcastically remarks making Rory glare at her while Lorelai and Michelle laugh.

Just as Rory was about speak Tristan cut her off. "Ladies, breakfast is served."

The girls joined them at the table and they all began to put food on their plates and eat. As they were eating Sienna turned to Charlotte.

"What are you going to say to Ursula when you go and see her?" Sienna asked making Rory and Lorelai stare at her waiting for her response.

"I am going to apologize for embarrassing her and hope that I don't get fired. I worked real hard just to get where I am and I'm not giving up." Charlotte said stabbing her food harshly with her fork.

"Well I am going by that way, I can drop you off if you want?" Austin offered not noticing the looks he was getting from Lorelai and Tristan.

"I can take Charlotte," Tristan added. "She and I have some things to discuss."

Charlotte was looking between the two and could feel the testosterone in the air. She had never been in a situation where guys were fighting over her. This was more Rory's expertise seeing as she went through this with Dean and Jess. Charlotte had to put a swift end to this before it got out of hand.

"I think I will take the train, not that it is not appreciated. I just need time to think about what I am going to say to Ursula." Charlotte said to Austin and Tristan.

Lorelai watched as her daughter defused the situation. She didn't know what the outcome of this love triangle was going to hold. All she knew was that someone was going to get hurt and she was hoping Charlotte didn't become a casualty.

"Mom when are you and Rory leaving?" Charlotte asked breaking Lorelai out of her thoughts.

"Trying to get rid of me already?" Lorelai mockingly question with a hand over her heart making her daughter laugh.

"No. So I can spend some time with you."

"We're not leaving until late tonight. Sookie and Michel are running the inn for me. Rory is not so busy with school at the moment. We can go to dinner and _talk_." Lorelai said with emphasis.

Charlotte saw the look on her mom's face and knew she meant business about dinner. She glanced at Rory and saw she was staring at her with a look of worry. Charlotte sent a small smile towards her making Rory smile back.

"This has been fun but I got to head to home," Ethan said getting up from the table. "Charlotte I will see you at school. Sienna you coming?"

"Give me a second, I'll meet you in the lobby," Sienna said watching as Ethan said goodbye to everyone and closing the apartment door behind him. Sienna went into the living room and gave Charlotte her camera. "These have all the photos from the hotel. The plans are in our office, can you print the photos so when I come in later, I can just organize everything?"

"Don't worry about it. I will put it in a folder and place it in the file cabinet by your desk. Now go and be with your boyfriend." Charlotte said hugging her friend before she said her goodbyes and walked out of the apartment.

Charlotte brings her dishes to the sink and picks up her jacket and bag. She then gets the camera and places it inside her bag. "I am leaving now. Mom I will call you when I'm on my way home." Charlotte said heading for the door.

"Ok Sweets. Good luck sucking up to your boss."

"Bye Mom," She said turning to Rory. "Don't let her go in my closet. I know how she gets when she sees clothes." She advises getting a laugh from Tristan, Austin, and Rory. Lorelai pouts at he daughter as the door closes.

(Time Skip)

Charlotte was typing away at her computer in her office. She had got to work and everyone was very busy. She had printed out the photos for Sienna earlier and had place them in the file cabinet for later.

As she was typing the office phone rang beside her. She picked it up and stopped typing.

"Underwood Designs." She greeted.

"Charlotte can you come to my office please. I feel there is things we need to discuss." Ursula said in a professional voice.

"Of course, I will be there in a few minutes."

"Thank You" Ursula said hanging up the phone on her end.

Charlotte stood from her desk and straightened herself as she walked towards Ursula's office. She noticed that several people stopped what they were doing. Obviously what happened at the hotel yesterday was spread throughout the office.

When she reached the door to Ursula's office, Charlotte knocked on the door waiting for a reply.

"Come inside Charlotte" Ursula said from behind the door.

Charlotte opened the door and her mood shifted instantly. Francine Hayden was sitting right next to her boss and Charlotte was getting angry all over again. She then reminded herself she worked to hard to get here and she was not going to let Francine or anyone get in the way of that.

"Please take a seat so we can get things underway." Ursula ordered.

Charlotte sat far away from Francine which Ursula noticed. Francine glanced at her granddaughter before taking a sip of her tea.

"Ursula I would like to apologize to you for embarrassing you last night. I was out of line and I hope this doesn't affect my future here working for you." Charlotte said looking directly at Ursula who had a non expressionless face.

"Is that all?" Ursula asked making Charlotte confused at the question.

"I'm sorry was their something else you wanted me to apologize for?"

"What about Francine? You rudely disrespected her and I believe she is owed an apology as well." Ursula casually said picking up her teacup.

"With all due respect Ursula but what happened between me and Mrs. Hayden has nothing to due with my job. I apologized for what I said and have caused to you. I am not apologizing for what I said to her." Charlotte said icily.

Francine and Ursula both looked at each other and put their teacups down. Ursula got up and walked to the door, "I will leave you two to talk. When I return hopefully we can salvage the goal of yesterday's meeting" Ursula said closing the door

"You must really hate me?" Francine said acknowledging Charlotte once they were alone.

"You can't hate someone you don't know. I may not like your ways and how you disregard things but I don't hate you." Charlotte said bitterly.

"So why do you treat me like I don't exist?"

"I treat you how you and your husband treated me the first time you met my sister and I. It hurts being treated like you don't exist. That has been my entire life when it comes to the mistake my mother and my sad of an excuse father made." Charlotte said indifferent

"I will say that I may not like how things have happened but you must understand that Straub and I had goals for Christopher. Although I regret the way we treated you and your sister, things happen for a reason." Francine said.

"What do you mean?" Charlotte said.

"I may not have ever been an active part of your life but I have asked about you. I know our relationship is strained but your grandparents have kept us informed of you and your sister achievements. The one thing I must say is, I admire the way you independently make moves.

"What do you mean?" Charlotte repeated.

"You have never asked for anything financial when it came to schooling or extracurricular activities."

"I have never like the fact that Emily and Richard think they could use money to control anyone. It may work for my Mom and Rory but not me. I have a lot of pride so no matter the hardships I go through I'd rather earn on my own." Charlotte reasoned.

Francine for the first time in her life really took a look at her granddaughter. She was inspiring to say the least and she would go far with the Hayden legacy, as well as the Gilmore legacy. In order for that to happen she would have to convince Straub. Lord knows The Hayden family were stubborn and Charlotte was the spitting image of Straub in this moment.

"I think its time we bring Ursula back inside so we can get down to business." Francine says heading to the door.

"Before we open that let me be clear with you on something", Charlotte said standing up from her seat making Francine stop at the door handle to look at her. "I'm willing to be cordial because my boss is my best friend. It will take me a very long time before I can willingly accept you into my life. I hope you understand where I am coming from?" Charlotte explains, letting go of Francine's hand.

(Time Skip)

Once Ursula walked back into her office they got down to business. Charlotte gave Ursula her mock up of how the exhibition would play out. To say Ursula and Francine were impressed would be taking it lightly.

Charlotte had spoken with Ethan's mother and the Dean of Student affairs to plan for the fashion exhibition. The entries would be fifty designers showcasing their work. Ursula and two of the professors at the school would be the judges. Charlotte would be working backstage with Rafael to get the models ready.

Charlotte had already taken the liberty of hiring a catering service courtesy of Sookie St. James. She had already handed the demo advertisement to Ursula to show her the color scheme. Ursula wanted a few minor adjustments, but all in all everything was managed to a tea.

After reviewing it once more Ursula put down the folder Charlotte had handed her. She folded her hands over the folder and gave Charlotte a pleased look.

"This is well thought out and planned Charlotte. I want you to make copies of these and give them to Rafael and Harper. After that meet me in the studio downstairs we have an important client remember" Ursula ordered with devilish smile.

"I thoroughly agree, Ursula. This is marvelous planning and I cannot wait to see it playout." Francine added.

Charlotte then realized once Ursula said important client that she forgot that Sarah Jessica Parker was coming here to pick out designs for a red carpet event.

"Right Away Ursula" Charlotte said walking out her office.

"And Charlotte." Ursula called out making the Gilmore rush back into her office.

"Yes Ursula?"

"If you ever embarrass me like that in public again, I will make sure you never work in the fashion industry in any capacity. Do I make myself clear?" She said sternly.

"Crystal"

"Run along now. I have a business to run." Ursula said making Charlotte rush down the hallway.

(Time Skip)

When Charlotte returned to her office she saw Sienna putting her bags beside her desk. Sienna looked up at her and ran up to her.

"How was the meeting with Ursula? Do you still work here?" She asked.

"Thankfully I do. The weird thing about it is I somewhat made peace with Christopher's mother Francine."

"Shut up!" Sienna exclaimed making people pass by look at them weirdly.

"Yeah I'm not gonna call her grandma or anything cause I don't know her that well but I could see us getting along better in the future."

"What does this mean for you and Christopher?"

"Honestly I really don't care if he is involved in my life. When I was younger I may have wanted that but now that I'm older I really don't feel the need to see him. For the longest he wasn't around and the things I needed him for Luke was there so I just need him to stay away."

"You know eventually you two are going to bump into one another." Sienna states.

"I will deal with it when the time comes. Until then we need to go downstairs to the studio." Charlotte said gathering her things beside her on the desk.

"Why? What's happening downstairs?"

"It seems like I am not the only one who forgot what we are doing today," Charlotte briefly stated heading towards the door. She turns around and says, "We are helping SJP pick out an outfit for a red carpet event and she is waiting with Ursula and I assume Harper down in the studio."

Sienna' eyes widen in remembrance before quickly scrambling to gather her things to follow after Charlotte.

When the girls reach the studio downstairs they see people running around. Over in the corner they see Ursula sitting at a small table drinking tea with Sarah Jessica Parker. As they got closer to them Ursula glanced at them. She beckoned them to come join them.

"Sarah I would like for you to meet my two newest interns Charlotte Gilmore and Sienna Miller." Ursula said standing up.

"It is pleasure to meet you Ms. Parker." Sienna said with Charlotte nodding in the background.

Trying to get things back on track, Ursula explains what the girls will be doing. "Okay girls, I need for one of you to take photos of the clothes she tries on. While one of you steams the clothes before and after she tries them on."

While Ursula led Sarah Jessica Parker to the changing room Charlotte picked up the steamer and started to steam several dresses. Sienna was taking a photos of all the clothes on the racks.

"I cannot wait for this day to be over with." Charlotte sighed in exhaustion.

Sienna glanced over at Charlotte and laughed. "How are you not excited that we are in the presence of Hollywood Royalty? I mean it is Sarah Jessica Parker. Does _"Sex & The City"_ not ring any bells?" Sienna said with excitement.

"You are too happy for me. I'm still dealing with the backlash of last night and the truce with Francine."

"Well don't forget you are going to have to talk about it tonight once more with your mom and sister." Sienna reminded Charlotte who slapped her forehead in agitation.

"Don't remind me. Ugh!", Charlotte put the steamer down and rubbed the side of her head. "Maybe things here will run smoothly and I have a huge idea. I just hope Ursula will ask."

"What are you talking about Charlotte?" Sienna asked in confusion.

Before Charlotte could reply to her friend, SJP came out of the dressing room with a vintage black chiffon dress. It had a silver sash that wrapped around the dress. To top the dress off she was wearing a pearl necklace.

"She looks gorg!" said one of the assistants by the photographer.

Charlotte agreed with that statement one hundred percent. In Charlotte's opinion the dress was simple and elegant but that soon changed with Ursula's comment.

"Its to safe darling, you need something with a pop of color. How about red to make it more edgy with a touch of white for the sophistication." Ursula offered.

When SJP came back out she wore a blood red dress. The dress was sleeveless and had a sweetheart neckline. Around her neck SJP was wearing a Diamond Choker, with a single diamond teardrop hanging from it.

This dress was significant enough to make Ursula put down her teacup and critique how it looked on SJP.

"Sarah this dress looks divine on your figure," Ursula stood up from her chair and began to circle SJP. "This is the dress you should wear to the premiere and I want you to have it. Keep it as a gift from me. Hopefully you will continue to come and model for me." Ursula said with a professional smirk on her face.

"Of course Ursula, I cannot thank you enough. If there is anything I can do let me know." Sjp said.

"Well there is actually." Charlotte said interrupting their conversation with Sienna trailing behind her.

"What may I ask are you talking about Charlotte?" Ursula asked sternly making Charlotte nervous.

"I hope you don't mind me asking if Miss Parker would like to be a judge with you for the designer expo?" Charlotte asked making everyone in the studio give her looks.

"What designer expo?" SJP asked curiously.

Charlotte, Sienna and Ursula then began to explain the details on the events that were in the planning stage. After they finished explaining everything SJP immediately agreed to be a celebrity judge.

"To help pick an upcoming designer display their work at the Underwood Gala Event would be a joy. Ursula call my people to set up a time and date when everything is finalized," SJP then turned to the girls. "I also want to thank you girls for all the help today. You guys will go far in this industry just work hard at it and your big break will come." She said walking out with the dress in a bag.

(Time Skip)

After SJP left Charlotte and Sienna cleaned up the studio. They had packed all the clothes and returned them to the storage center within the building. Sienna was going to the hotel with Ursula and the rest of the development team. Ursula had let Charlotte leave early since she came in earlier.

Charlotte quickly jumped inside a taxi and twenty minutes later she was in front of her Apartment. She gave the driver his fare and ran inside the building. Charlotte waved to Mr. Jone as she rushed onto the elevator.

As the elevator doors closed Charlotte pressed the number to her apartment level. She rode the elevator for a few moments and the doors opened to Austin kissing a blonde girl. To say Charlotte was shocked, was saying it lightly. Just last week he asked her out and now he was kissing some other girl.

Austin stopped kissing the girl and noticed Charlotte standing in the elevator. He pulled away from the girl quickly almost making her topple over.

"Hey Charlotte" He said awkwardly.

"Hi Austin", Charlotte replied before turning to the girl standing next to him. "Who's your friend?" She asked making him nervous.

"Hi I am Monica. Me and Austin go way back", Monica said sultry to Austin before entering the elevator. "I'll call you later and Charlotte it was nice to meet you."

When the elevator doors closed the two of them stood in the hallway until Charlotte walked towards her apartment door.

"So you have nothing to say?" Austin asked making Charlotte stop walking to face him.

"Why would I say anything? We weren't in a relationship to begin with. All I can say is I find it funny." She calmly said.

"What do you find funny?"

"It's funny because I remember you asking me out at your party", Charlotte moved a strand of hair behind her ear before continuing. "Then literally five minutes ago you were kissing whatever her name was. Maybe I was just some notch on your belt or something? Who knows maybe its for the best anyway."

"Come on Charlotte she didn't mean anything." Austin said making Charlotte give him a small smile that made him feel guilty.

"The sad part is I believe you when you say that. That gives me even more of a reason to move on. Anyway I am kinda exhausted so I will see you around." Charlotte said opening her apartment door and quickly closing it leaving Austin alone in the hallway.

Charlotte hangs her coat and purse by the door and walks further into her apartment. She sees her mom and Rory watching TV with Tristan and Michelle.

"Hey Char how was work?" Michelle asked moving over to make room for her best friend.

"Exhausting but so worth it. We got help Sarah Jessica Parker pick out a vintage dress and she has agreed to help out with the Fashion Expo at FIT. So basically everything is falling into place." She explained.

"You met Carrie Bradshaw!?" Lorelai exclaimed in awe.

"Mom that is just a character she plays. But yes I met her and she is so kind and sweet."

"Was she speaking in third person?" Lorelai joked making all the teens laugh.

"No she wasn't but that's not all that happened today. Francine and I finally came to an understanding." She added while Rory and Lorelai gave her confused looks.

"What does that mean?"

"It means I am willing to give her a chance. We're not gonna be buddies but I can be cordial around her. I can tolerate her more than Emily and that says a lot." Charlotte remarked.

After the words came out of Charlotte's mouth, Lorelai was in shock. She never thought Charlotte of all people would get along with the Hayden's before her own parents. It was no secret Charlotte and Emily did not get along. It made Lorelai weird and thankfully Rory asked the question she so dearly wanted to ask.

"How can you actually be able to sit down with Francine but not Grandma?" Rory asked.

"Emily likes things done in a proper way and nothing can be out of the ordinary. Not that Francine is not the same way but she at least explained to me why she acts the way she does. In some sort of way I can understand where they are both coming from. That doesn't mean I will be trying to be around Emily in the near future."

"I was afraid you were going to say that" Lorelai said.

"What did you do?" Charlotte accused making Lorelai wince.

"I may have sort of invited you to be my plus one to the Yale-Harvard game." Lorelai attempted to say in sweet voice.

"Yeah that's not happening unless you want me to make a scene on the campus," Charlotte turned to her sister. "No offense"

"None taken." Rory said before continuing. "I told her when we left their house at dinner you were gonna be pissed."

"I'm not mad actually since I won't be going."

"I have a better proposal." Tristan added finally entering the conversation.

"What might that be Bible boy?" Lorelai asked.

"Well since I am going to the game with my grandfather I was actually going to invite you Char." He offered with a smirk.

"Ok" she simply said heading into the kitchen.

As she walked into the kitchen she heard several footsteps behind her. When she tried to open the fridge a hand pressed on the door. She turned to see her mom and sister behind her staring at her with quizzical looks. Tristan was smiling at the antics of the Gilmore Girls standing in the back of them watching everything.

"What?"

"All it took for pretty boy was to ask you and you say yes?"

"Yup." Charlotte said emphasizing on the p.

"What does he have that we don't?" Lorelai whined jokingly.

"He kisses real good and he has killer blue eyes you get lost in." Charlotte gushed.

"But now I'm gonna be stuck with my parents and you were going to be my buffer."

"You have Rory I will probably come and say hi to you, but I won't be staying unless you want your mother's burial plot to be apart of Yale's history" She added watching Rory give her a disapproving look while Lorelai hugged her daughter.

"Bless your sweet, sweet heart. Only you would save mommy from the overbearing Grandparents." Lorelai ranted in a mad chant.

"Then what do I do when we go to dinner with them?" Rory asked.

"Suck up to them" Lorelai said cheekily.

Charlotte and Rory laughed at their mothers antics with Tristan and Michelle shaking their heads the entire time.

(Time Skip)

Charlotte was packing her bag for school the next day. She had just finished having takeout with Her mom, Rory, Michelle, & Tristan. Tristan had left already, he had a meeting with his father in the morning and he said he would call her tomorrow. Rory and Michelle went to the store to get some things.

Charlotte turned to her doorway and saw her mom staring at her. She had seen the same look over the years when her mom was worried about her and Rory.

"I know we need to talk about what happened with me and Christopher."

"Yes we do." Lorelai said walking further into the room.

Charlotte watched as her mother sat on her bed then joined her. She knew this was something she did not want to talk about.

"I know I may not have lead the best example when it comes to your father but he is still your father at the end of the day." Lorelai started.

"Mom what will it take for any of you to understand you can't make excuses for a grown man. You have always gave him and opening to be in our lives. He always took it for granted and I now know I can never depend on him in the way I need for him to be." Charlotte stated.

"Why haven't you said this from before?"

"He hurt me a lot over the years so now I want nothing to do with him.

"You cant cut your dad-" Lorelai began to say before Charlotte cut her off.

"He is not my dad or my father. His name is Christopher. He doesn't deserve the title. A dad is someone who is there and frankly he chose not to be there. Like I told him, whenever I think of the word dad I think of Luke. Luke was there and he didn't have to be but he was. He taught me how to ride a bike, how to cook and play baseball." Charlotte said with wiping her eyes as tears fell.

Lorelai pulled her daughter into a hug. To hear all the anger resentment and pain coming from her daughter made her realize the mistakes Christopher had made. He had truly ostracized himself out of Charlotte's life.

"Charlotte what would it take for you to let him in to your life?"

"Nothing. I already told him I dont want him in my life. Just worry about Rory and your new daughter."

"Charlotte you don't mean that. You need your dad in your life." Lorelai said.

"Mom I know you want me to have a relationship with him but I am over it. I will probably have another meltdown if he tries to talk to me. So I need for you and Rory to respect my wishes and tell him to stop asking about me. Keep any mention of me away from him." Charlotte said going back to packing her bag.

"One day you are going to regret not giving him a chance." Lorelai said.

"He's the one with regrets. I remember you speaking to him just after Rory got into Chilton. You told him that the door is always open whenever. I realized right then and there that if he truly cared about us, we would be his number one priority. Now he has a second chance with his new daughter. Hopefully she gets the dad Rory and I were supposed to have." Charlotte said.

Charlotte finished packing up her bag and placed it beside her nightstand. When she put it down she saw the box from the night before. She picked up the box and brought to her mother.

"He sent this to me last night. I wondered how he got my address?" Charlotte questioned to herself.

"That would be my doing. He has a right to know what you are doing with your life Char. No matter how hard you push he is going to ask about you."

"I am not repeating myself anymore. Can you take this box back to Stars Hollow with you?"

"Sweets you can't keep going on like this." Lorelai said

"Then what do you suggest I do Mom?"

"Talk to your father."

"It doesn't get anywhere because he doesn't understand." Charlotte said walking out of her room.

"You can't keep pushing it away it will keep following you."

"Well you are the expert Mom." Charlotte said.

"What is that supposed to mean?" Lorelai asked her daughter who turned to look at her.

"Correct me if I am wrong, didn't you run away from your parents because you felt like they didn't understand you. Hell you barely like to speak to them as it is. What is so different from what I am doing compared to what you did?"

"I left because I wanted live my life the way I wanted. I was 16 with two babies and I didn't know what I was doing. All I knew was I had to be different from my parents but I couldn't do that with them in control of everything. Next time you say something have the facts behind it."

"Sorry Mom just talking about him makes me angry."

"I get it so here's what I am gonna do. I am going to setup a sit down with Christopher so both of you can get things off your chests. This time no flipping out just try to listen and react differently."

"I will act accordingly with the situation how I see fit. So I will try my best not to flip out."

"That's all I ask" Lorelai encouraged.

"Do you always feel like this after you go to those Friday night dinners?"

"Worse." Lorelai said with a pout.

This comment gained a laugh from Charlotte making Lorelai smile. Hopefully things at this sit down will help heal the relationship between Christopher and Charlotte, otherwise she didn't know what to do.

(Time Skip)

Charlotte was sitting on the roof of her building watching the city lights. When Rory and Michelle returned, Lorelai and Rory had to leave to get back to their lives. It made her miss them each time they saw each other.

The only good thing that came from these last couple of days was the truce with Francine. Charlotte didn't know what to expect when it came to the Haydens but she knew she was going to be cautious. When it came to high society people Charlotte knew they always had a ulterior motive, so she was going to keep her at a distance.

She still was kinda wary of the sit down that her mom was planning with Christopher but she had no expectations. To Charlotte he was always going to let her down and she was over it. The feeling of being constantly being let down and disappointed was exhausting. She wondered why it was easier for her mom to grow up but not him.

"Char" a voice said breaking her chain of thought.

Charlotte turned around and saw Michelle with two mugs. She approached her best friend and sat down next to her.

"Thanks" Charlotte said as she took the mug and sipped some of the coffee.

"I figured you wanted to be alone."

"What would I do without you Michelle? I think beside Rory and Jess you are the only person who understands the things I am going through when it comes to daddy issues."

"Of course I understand but I don't let it define who I am. You cannot have your personal life affecting your professional life. You're very lucky not to be fired and I hope this taught you something." Michelle said.

"It did."

"What exactly are you going to do now that all of your problems erupted."

"To be honest I have to deal with it day by day. I'm trying for it not to drown me but it seems like I am sinking." Charlotte said placing the mug beside her.

"Well only time can tell and I need to ask you about Austin." Michelle aid changing the subject.

"Austin?"

"Yeah, what is going on between the two of you. I thought you and Tristan were working on something?"

"Oh I totally forgot to tell you what happened when I came home earlier." Charlotte said explaining about the incident in the hallway.

"Wow."

"I mean I wasn't surprised. Plus things with Tristan are good for now and I don't want to ruin that." Charlotte explained.

"Didn't he just ask you out?"

"Like you said to me all those years ago, Men always think with what's in between their legs then their brain" Charlotte quipped making the girls laugh.

"Come on we have a new day for more problems." Michelle said helping her friend up from and the two girls walked back inside.

(Time Skip)

Charlotte had a long day in school and sitting in several lectures she knew she was exhausted. Walking down the street Charlotte stumbled upon a music shop. It seemed lively with several instruments around with customers browsing around. Charlotte hadn't touched a piano since her weekend in Stars Hollow.

She entered the shop and looked around until she saw what she was looking for. She walked directly to the object of her sight. The piano in front of her was perfect with the black gloss gleaming in the fluorescent lighting. Charlotte pulled the bench out and sat down on it.

"We just got this one in earlier this week. It's beautiful isn't?" A man said as he approached Charlotte.

"Yes it makes me feel at home whenever I touch the keys." Charlotte said with a smile.

"Do you play?" He asked curiously.

"Why don't I show you and you can see if I play well or not." Charlotte added.

Charlotte begins to play a couple of keys gaining the attention of several customers. The man picks up a guitar and strums it and begins to play alongside her.

 _Da da da da_  
 _The smell of your skin lingers on me now_  
 _You're probably on your flight back to your home town_  
 _I need some shelter of my own protection, baby_  
 _To be with myself and center_  
 _Clarity, peace, serenity_

 _I hope you know, I hope you know_  
 _That this has nothing to do with you_  
 _It's personal, myself and I_  
 _We've got some straightenin' out to do_  
 _And I'm gonna miss you like a child misses their blanket_  
 _But I've got to get a move on with my life_  
 _It's time to be a big girl now_  
 _And big girls don't cry_

 _Don't cry_  
 _Don't cry_  
 _Don't cry_

 _The path that I'm walking_  
 _I must go alone_  
 _I must take the baby steps till I'm full grown, full grown_  
 _Fairy tales don't always have a happy ending, do they?_  
 _And I foresee the dark ahead if I stay_

 _I hope you know, I hope you know_  
 _That this has nothing to do with you_  
 _It's personal, myself and I_  
 _We've got some straightenin' out to do_  
 _And I'm gonna miss you like a child misses their blanket_  
 _But I've got to get a move on with my life_  
 _It's time to be a big girl now_  
 _And big girls don't cry_

 _Like the little school mate in the school yard_  
 _We'll play jacks and Uno cards_  
 _I'll be your best friend, and you'll be mine_  
 _Valentine_  
 _Yes, you can hold my hand if you want to_  
 _'Cause I want to hold yours too_  
 _We'll be playmates and lovers, and share our secret worlds_  
 _But it's time for me to go home_  
 _It's getting late and dark outside_  
 _I need to be with myself and center_  
 _Clarity, peace, serenity_

 _I hope you know, I hope you know_  
 _That this has nothing to do with you_  
 _It's personal, myself and I_  
 _We've got some straightenin' out to do_  
 _And I'm gonna miss you like a child misses their blanket_  
 _But I've got to get a move on with my life_  
 _It's time to be a big girl now_  
 _And big girls don't cry_

 _Don't cry_  
 _Don't cry_  
 _Don't cry_

 _La da da da da da_

Clapping erupted after the last note was sung making Charlotte look around the room and grin. She stood up from the stool and took a cute curtsy gaining more cheers.

"My dear you have a talent. I never introduced myself, the name is Gary Sutherland and I am the owner of this establishment."

"It is nice to meet you Mr. Sutherland. My name is Charlotte Gilmore you have a lovely store." Charlotte complimented while gazing around the store.

"Thank you Charlotte. Now I wouldn't want anything such as your raw talent to go to waste so I have something to offer you." Mr. Sutherland said gaining the attention of Charlotte.

Mr Suther land walked away and when he noticed that Charlotte wasn't following him, "Aren't you coming?"

*The next chapter will be titled "James Dean Needs A Place To Stay" and the following Chapter will be titled "Ted Koppel's Big Night Out"

*The song(s) are a follow

 _"Big Girls Don't Cry" by Fergie_

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	11. James Dean Needs A Place To Stay

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS**

The Life & Times of Charlotte Gilmore Chapter 10: James Dean Needs A Place To Stay

Charlotte followed Mr. Sutherland into his office and watched as he sat down at his desk.

"Young lady you have raw talent when it comes to the piano. I haven't seen anyone touch keys like that since my wife. Where did you learn to play like that if you don't mind me asking?"'

Charlotte paused for a moment before she spoke, "When I was about nine years old my father had missed my birthday party. He was always missing anything important that had to do with my sister and I. So his apology came in the form of a piano. At first I wanted nothing to do with it until I was watching some award show and I saw Alicia Keys playing one of her songs. To think I had the same instrument in my own home."

"Who taught you to play?"

"My mom paid for me to have lessons. For weeks I practiced until I thought I was ready to play in front of people. I entered a contest in my hometown and I was nervous but I did it. I earned third place and for once I had something no one could take from me. Music has always been that thing for me to let go of the negative emotion I was feeling in that moment." Charlotte explained making Mr. Sutherland lean forward in his chair.

"You look like someone who has been trying to find a way to say something without saying it. Music is that way for you, so here is what I am going to do. I am gonna let you have that piano out there."

Charlotte was surprised at this man's offer. She had only met him fifteen minutes and he was giving her the top of the line piano. What exactly did he want in return?

"What's the catch?" She asked curiously

"You remind me of my wife", Mr. Sutherland said looking weary just talking about her. "She passed away a couple of years ago. You play the piano just like her and it brings me back to every time she played. Those memories are something I will always cherish. She was passionate about music and you have that passion. I see it in your eyes and I want that to continue."

"Thank you Mr. Sutherland. I haven't heard someone spoke that much conviction whenever I play the piano. The only person who has always been in my corner is my mom and friend. I don't know yet but I'll see." She said walking out of the until Mr. Sutherland spoke one more.

"Just think about it kid" Mr. Sutherland offers giving Charlotte quite a lot to think about.

(Time Skip)

It was late at night when Charlotte was sleeping until she heard her phone ringing. She looked at the alarm clock and saw it was three in the morning. She picked up her phone and saw it was Jess.

"Why are you calling me so late?" She answered groggily.

"Can you come and pick me up at my apartment?" Jess said annoyed.

"Jess do you know what time it is? I have a very long day in the morning and I need sleep."

"My apartment building caught on fire and I have no place to stay. I wouldn't call unless I really need to."

"Jess are you ok? Did you get burned or anything? Do you need to go to the hospital?

"You Gilmore's sure know how to ramble. I am fine I am standing outside the remains of my former home. There are cops, paramedics and firemen everywhere. Just let me know when you will be here." Jess said.

"Give me twenty minutes and I will be there soon."

"Thanks Charlotte. I didn't know who else to call but you." Jess said softly.

"Like I told you, I got your back now im a getting dressed. I will call you when I am there."

"Alright." Jess said hanging up the phone.

Charlotte got out of bed and when to Michelle's room. She knocked on the door and few minutes later Michelle opened the door with a glare. Charlotte smiled at her best friend innocently making Michelle's glare harder to look at.

"Yes?" She responded grouchily.

"Can you come with me to pick up Jess?" Charlotte asked as Michelle folded her arms across her chest.

"What's wrong with him now?" She asked tiredly while yawning.

"His entire apartment building is on fire and I said he could stay here. He has know where else to go. You know I wouldn't offer unless it was really important."

Michelle scratches her head and grumbles saying "Go and get ready. Make sure there is coffee, lots and lots of coffee." She orders closing the door. Charlotte puts a pot of coffee on and head back inside her room to get dressed.

Ten minutes later both girls are dressed and have to go cups of coffee. They grab their jackets and head for the door.

(Time Skip)

Charlotte parked the car a block away from what was Jess's old apartment. Beside her Michelle was snoring. She had been complaining since they left their apartment about being woken up early. Charlotte was thankful she passed out after a while. She looked at her phone and dialed Jess.

"Where are you? She asked when he answered.

"I am around the corner in a café."

"Stay there I am coming too you." She said hanging up the phone. Charlotte nudged her sleeping friend.

"What now?" Michelle voiced sleepily rubbing her eyes.

"I am going to get Jess from this café around the corner."

Michelle gives her travel mug, "Get me a refill and a muffin."

"As you wish" Charlotte quips getting out of the car.

She walks down the street passing the scene of the fire. Charlotte finally sees the café and enters. Looking around she finally notices Jess in the corner. Just looking at his appearance, Charlotte could see her friends annoyance and exhaustion. She walked up to his table getting his attention. He was drinking tea from what Charlotte could tell.

"Hey" Jess said.

Charlotte pulled him up from his chair into her arms. "I am glad you are ok. Do you have anything with you?"

"Just my bag that I had with me. I was at work when all this happened. Most of the stuff in there was junk anyway." Jess said nonchalantly.

"I'm just happy my rebel friend is alive" Charlotte joked with Jess rolling his eyes. "Come on Michelle is waiting in the car and just to warn you she is really grouchy." She said leading him out of the café.

"Oh Joy" Jess remarked sarcastically.

"Did you call Luke?" She asked as they approached the car.

Jess stopped walking when they reached the car. You could see the range of his emotions on his face until it quickly disappeared. That was one of the things she hated about Jess. He could be open one second and locked up tighter than Fort Knox the next.

"No I didn't. I don't even think he wants to hear from me anyway."

"Maybe if you actually called you could find out." She said vaguely as they enter the car jostling Michelle awake once more.

"For the love of god can you both shut up!" Michelle exclaimed irritatedly making Charlotte and Jess laugh at her. She grumbles then rolls over facing the window.

"Let's go home." Charlotte said after everyone settled. She turns on the car and begins to drive away from the scene. As they are driving Charlotte looks in the rearview and sees Jess looking out at city lights. She then glances over to Michelle, who has once again started to snore.

Eventually they pull up in front of the apartment building. The trio walked into the lobby running into Mr. Jones.

"Ladies you are out awfully late" He said with a smile.

"Yeah we had to pick up my friend and he is going to be staying with us for a while. We were wondering if you had spare key to our apartment so he could come and go as he pleases?" Charlotte asked the manager.

"I think I might, give me a minute to check." Mr. Jones said turning to check his office.

While Mr. Jones was looking around for the spare key, Charlotte turned to Jess. "Have you decided if your going to call Luke or not?"

"Huh"

Charlotte glared at the boy beside her as he became monosyllabic once again. "I can do this all night. Either you call Luke or I call my mom making all of Stars Hollow know your current situation." Charlotte threatened making Jess glare right back.

"You wouldn't dare" he growled.

"Try me" she added just as Mr. Jone came back to them.

"Here is the spare key to your apartment. Let me know if you need anything else" Mr. Jones advises before going back to his office.

"Can we go upstairs now? I miss my bed and you two are getting on my nerves. Jess call the diner man so she can stop talking.", Michelle then faced Charlotte. "And you stop badgering him to do something he is obviously not comfortable doing" she ranted before heading to the elevator. Jess and Charlotte looked at each other and nodded before following after Michelle.

A few minutes later, Charlotte opened the apartment door with Michelle and Jess right behind her. Michelle tiredly walked into her room closing the door right behind her.

"Do you think she is pissed for waking up early?" Jess asked as he sat down on the couch.

Charlotte smirk before saying, "She will be fine after a good night's sleep. I am going to get you some sheets and a comfy pillow. The couch pulls out into a bed so set it and get comfortable."

Charlotte walks into her room and pulls off one of the pillows off her bed. She then walks into her closet and grabs a comforter.

"Thanks again for letting me crash here." Jess says as Charlotte walks back into the living room.

"No thanks necessary. I would not leave you in the street to fend for yourself. Nor would you do the same to me", She hands him the sheets and pillow as she walks back to her room. She turns around to look at him once more. "Night Jess".

"Night Charlotte" he says as he lays down.

(Time Skip)

Charlotte was waiting in front of Underwood Designs for Tristan. He had called and said he would pick her up and take her to dinner. She really needed it after the long day she had. Between setting up the expo and Gala event, things at work were very stressful. Charlotte was very hopeful things went on without a hitch.

Charlotte heard Tristan's car stop in front of her. He got out of the car with a bouquet of flowers and his trademark smirk.

"Hey Beautiful." He greeted with a kiss on her cheek.

"Hi Tristan", She returned and took the flowers he gave her. "These are perfect, Tristan."

"Come on you must be hungry" Tristan said leading her to his car. He opened the door for her and watched as she got in the car. He then ran to his side of the car and entered. He looked at her and smiled and started his car.

"You look tired Charlotte. Is everything okay? Are you still worried about that sit down with your dad?"

"No it has nothing to do with him. Last night Michelle and I had to go and get Jess. His apartment building caught on fire, so I said he could stay with us."

"Remind me who Jess is again?" Tristan said as the car stopped at a red light.

"He was Rory's boyfriend right after Dean and a good friend of mine. I was in a dark place after you left and he helped me let go of the pain. Its thanks to him I am able to be see things differently. So I consider him one of my good friends besides Michelle."

"Maybe I can meet him sometime."

"I think I want to keep you two apart just a little longer" Charlotte remarked.

"Why is that Char?"

"You both have this 'badboy' thing and you both can't stand Dean. If that doesn't forge a friendship, I don't know what will." She remarked making them laugh.

As they were laughing, Charlotte's phone began to ring. She looked at the Caller-ID and saw it was Mother.

"Are you going to answer it?" Tristan asked as his eyes were on the road.

"It's my mom."

"I don't mind if you answer Char. I like your mom and if you ignore it she is going to keep calling.

"I know that but I just wanted to be with you for a little longer without any interruptions." She added picking up the phone. "Hi Mom."

"Charlotte I heard about your new roommate and I am sad you didn't tell Mommy" Lorelai whined over the phone.

"How did you hear about it?"

"Jess told Luke, Luke told me. Are you sure your okay with Jess staying with you and Michelle."

"I wouldn't have offered my couch if I didn't think so. Does Rory know that he is staying with me?"

"Nope and that is between the two of you. Also I have spoken to Christopher about the sit down." Lorelai said changing the subject.

"And what did the flake say Mom? Did he have some excuse as to why he won't make it?" Charlotte asked agitated after each question.

"I'm sorry sweets." Lorelai said apologetically.

"I told you I don't have high expectations when it comes to him. To be honest this just proved my point even more. He only shows up when it seems best for him. I am tired of feeling like I am the one who has done something wrong" Charlotte sighs and glances at Tristan as he parks the car in a parking lot. "I will call you tomorrow Mom and thanks for trying anyway".

"Okay Charlotte but if you need anything I will come running."

"I know, bye Mom"

"Bye Sweets" Lorelai says as she hangs up.

Charlotte stares at her phone and then puts it back in her purse. She notices Tristan is staring at her with worry.

"Where are we eating?" She asks trying to get her mind off the conversation she just had with her mom."

"Over there" Tristan replies point at a restaurant across the street. They both get out of the car and head inside the restaurant. They are soon seated and looking at the menu. Soon a waitress came to their table.

"Hi my name is Heather and I will be your waitress for this evening. Can I interest you in the special?" She said seductively to Tristan.

"He's fine" Charlotte sniped at Heather who glared before walking away.

Once Heather was gone Tristan started to laugh at Charlotte's face. He couldn't believe she was jealous of the waitress. Yes the waitress was cute in Tristan's opinion but he only had eyes for Charlotte.

Tristan put his hand over Charlotte's making her forget her jealousy for the moment. "I want you to know that I am here with you."

"I know that" Charlotte said blushing.

"Charlotte you mean a lot to me and I would hate for something like that to get in the way. It has take us two years to get to this point. I was stupid and I let you go, now I have a second chance." Tristan said getting up from his chair kneeling in front of Charlotte.

"What are you doing?" Charlotte asked nervously as Tristan gazed into her eyes.

"I don't want to mess things up again between us. You saw something in me that I didn't know was there and you make me happy. Rarely in life do I ever get out of my comfort zone, until I met you", Tristan pulled a locket out of his pocket and placed it in her hands."So Charlotte Marie Gilmore will you do me the honor of being my girlfriend again?"

Tears had sprung out of Charlotte's eyes at Tristan's confession. She opened the locket he gave her and saw a picture of them. It was of their first date, when they went to the movies. She didn't know that a photo of them had been taken.

"Yes, I will be your girlfriend" Charlotte said pulling him to stand up. She put her arms around his neck while Tristan put his arms around her waist. The moment their lips met it was like fireworks going off. Since the moment they met, Charlotte always got goosebumps whenever she and Tristan kissed. This time was no different for her.

When they pulled apart Tristan was smiling at her. He was happy that she was his girlfriend once more. He also knew they had a lot of things to work out but he was happy in this moment.

"Just so you know," Charlotte adds getting his attention. "I will kill you if you leave without saying anything. Last time was because it was out of your hands, but you better not let anything stop you this time." She finishes kissing him once more.

(Time Skip)

After dinner Tristan and Charlotte stopped at an ice cream parlor and sat on a bench. They had a good time until they saw the time. Charlotte invited Tristan to stay the night and he agreed. Soon Charlotte was opening the door to her apartment with Tristan behind her. When the door opened Charlotte was not pleased. The whole place looked a mess and the only thing Charlotte could say, "JESS!"

Jess walked out of Charlotte's room and smirked making her more angry.

"What the hell did you do to my apartment?"

"I was making myself comfortable." He said nonchalantly picking up his clothes to make room for himself as he sat on the couch. He noticed the blonde guy

Charlotte was this close to strangling her friend. She knew he was a slob but this was ridiculous. Tristan could see Charlotte was about to explode so he pulled her into her bedroom. He placed her on her bed so she could cool down.

"Do you think if I put you back out there you won't rip his head off?"

"I'll try but tonight was so good but to come back to this.." Charlotte sighed walking back out into the living room.

Jess was attempting to clean up the mess when she sat on the couch. Tristan sat down next to her and watched as Jess joined them.

"Listen I'm sorry about the mess." Jess said apologizing.

"I get it Jess, believe me." Charlotte said cutting him off with a smile.

"Hey I'm Tristan" Tristan said introducing himself.

Jess looked at him with scrutiny and then glanced at Charlotte before nodding at him "Jess."

"Charlotte told me a little about you and I got to say I am not that impressed," Jess remarked before Charlotte hit him in the arm. "Ow, I was kidding, jeez. Anyway just don't hurt her. I have seen her at her highs and lows." Jess threatened.

"Believe me I am in it for the long haul and I will try not to hurt her" Tristan added.

Charlotte was happy that the two of them could get along. Her best guy friend and her boyfriend. If only Rory was here to see this. Charlotte looked at Jess and could see he knew exactly what she was thinking about.

"Where's Michelle, Jess?" Charlotte asked.

"She went out with some guy she met at a party. She told me to tell you that she would back late." He told her as he went up and continued cleaning.

Charlotte turned on the television and saw they were recapping the awards from the night before. She saw one of the reporters interviewing SJP.

 _"What are you wearing if you don't mind me asking?" The reporter questioned._

 _"I am wearing a vintage couture dress from Ursula Underwood. I was lucky that she had it. We went through several choice but ultimately she wanted me to wear something more edgy."_

 _"Well I must say it fits the part._

 _"It certainly does and also I will also be helping Ursula with a special event tied to her Underwood Gala. I would also like to give a thank you to her interns Charlotte and Sienna for the opportunity." Sarah Jessica Parker said walking back on to the carpet._

Charlotte was staring at the television in shock. Did Sarah Jessica Parker thank her on live television? Charlotte looked at Tristan and Jess as they both had the same expression as her on their faces.

"Oh my god!" Charlotte exclaimed rushing off the couch to get her phone. She quickly dialed her Mom.

"House of Liquors, what's your brand?" Lorelai asked jokingly.

"Mom, SJP just gave me and Sienna shout out on the red carpet. I didn't even think he would do something like that. She talked about the dress that Ursula picked out and then talked about the event I am planning for the Gala. Then she said our names," Charlotte ranted while Tristan and Jess watched her fan out.

"Charlotte that is great. Carrie Bradshaw said your name. My baby is going to be rich and then she can pay for someone to change mommy's diapers when she gets old. I knew you were mommy's favorite." Lorelai said in a crazed rant.

"I'll be sure to let Rory know that when I call her next." Charlotte quips.

"Mommy doesn't like that kinda talk"

"Mommy should stop talking in the third person before I call her mommy to fix her."

"Your mean."

"Still this will generate even more buzz for the expo. Is Sookie still catering for me by the way?"

"Yes she is. She and I will be there front and center."

"Thanks again Mom."

"Its no problem Char, and about earlier I am sorry."

"I don't blame you so it's water under the bridge. I will call you later on this week."

"Bye Sweets" Lorelai said hanging up.

Charlotte put her phone down and looked at the two guys. "I am hungry let's order Chinese."

"We just ate dinner not even an hour ago" Tristan said getting head shakes from Jess and Charlotte.

"After all these years you still question my eating habits. Have you learned nothing form dating me? Gilmore's are always hungry." Charlotte said picking up the phone once more. "Yes, I'd like to place an order."

(Time Skip)

The next night Charlotte and Jess decided to get out of the apartment and walk around. Jess was gonna show her this band that was playing tonight. Tristan, Michelle, Sienna, and Ethan were going to meet them there."

"What's the name of this band again?" Charlotte asked as they were waiting on line to get inside the club.

"Don't remember." Jess said getting an eye roll from Charlotte.

"How do you not remember the name of a band?"

"I met the guy in California and he told me he was playing here tonight, so I said I would come check it out." Jess explained vaguely just as Sienna and Ethan showed up.

"You are hiding something and I don't like it." Charlotte said to Jess while hugging her friends.

"Charlotte I still can't believe she said our names" Sienna said hugging Charlotte, with Jess and Ethan rolling their eyes at the girl talk.

Last night while Charlotte, Jess and Tristan were waiting for the food, Sienna called excitedly about SJP on the red carpet. They talked for an hour on what they would do when they became famous. To say the least Tristan and Jess wanted to strangle themselves to death.

"You're seriously not going to tell me who is playing?" Charlotte questioned once more.

"It's a surprise so stop pouting" Jess said with his signature smirk.

Charlotte getting bored from waiting on line looked around at all the people waiting and saw Tristan looking around.

"Ill be right back. Can you watch my spot?" She asks Sienna who nods. Charlotte walks over to Tristan and kisses him.

"Now that is a way to greet someone" Tristan said once they pulled apart.

"I am glad you think so. How was work?" SHe asked as they walked towards their friends.

"Really great since Dad let me in on a case." Tristan said happily.

Charlotte of course knew how things between Tristan and his family were. The relationship was at best hostile and her first impression of Mr. Dugrey, he was a complete ass. And Charlotte had met her full and she dated one, and was friends with one. Ass holes seemed to be the standard in being her friend.

They soon reached the front of the line and they were let inside the club. Jess led them towards the upstairs level and they all sat down. Michelle soon shows up and joins them.

"Sorry I'm late did it start? She asks as she sits down next to Ethan who is talking with Sienna and Jess.

"No and James Dean over there won't tell me who's playing " Charlotte replied annoyed.

"Don't worry you'll probably know who it is very soon" Michelle said taking her jacket off.

Charlotte saw the lights were beginning to dim in the club as a guy walked on stage. She realized the guy walking on stage was Austin. "Ladies and Gentlemen it gives me great pleasure to introduce the latest artist to the label. Dave Rygalski." Austin said as the crowd applause while Dave came on stage.

"Dave Rygalski?" Charlotte asked turning to Jess who had his smirk on his face. "Isn't he Lane's ex?"

"We ran into each other in Venice Beach. He was playing his guitar on the boardwalk and we got to talking. Since then we've kept in touch especially when he told me he got signed to a label out here in New York. So he called me up and invited me to his showcase." Jess explained.

"I think that is the most I have ever heard you speak James Dean." Michelle stated with Jess rolling his eyes.

They all turned their heads towards the stage as Dave and his band began to play:

 _I'm not a perfect person_  
 _There's many thing I wish I didn't do_  
 _But I continue learning_  
 _I never meant to do those things to you_  
 _And so I have to say before I go_  
 _That I just want you to know_

 _I've found a reason for me_  
 _To change who I used to be_  
 _A reason to start over new_  
 _And the reason is you_

 _I'm sorry that I hurt you_  
 _It's something I must live with everyday_  
 _And all the pain I put you through_  
 _I wish I could take it all away_  
 _And be the one who catches all your tears_  
 _That's why I need you to hear_

 _I've found a reason for me_  
 _To change who I used to be_  
 _A reason to start over new_  
 _And the reason is you_

 _And the reason is you_  
 _And the reason is you_  
 _And the reason is you_

 _I'm not a perfect person_  
 _I never meant to do those things to you_  
 _And so I have to say before I go_  
 _That I just want you to know_

 _I've found a reason for me_  
 _To change who I used to be_  
 _A reason to start over new_  
 _And the reason is you_

 _I've found a reason to show_  
 _A side of me you didn't know_  
 _A reason for all that I do_  
 _And the reason is you_

The band then played;

 _Your subtleties_  
 _They strangle me_  
 _I can't explain myself at all_  
 _And all that wants_  
 _And all that needs_  
 _All I don't want to need at all_

 _The walls start breathing_  
 _My mind's un-weaving_  
 _Maybe it's best you leave me alone_  
 _A weight is lifted_  
 _On this evening_  
 _I give the final blow_

 _When darkness turns to light_  
 _It ends tonight_  
 _It ends tonight_

 _A falling star_  
 _Least I fall alone_  
 _I can't explain what you can't explain_  
 _Your finding things that you didn't know_  
 _I look at you with such disdain_

 _The walls start breathing_  
 _My mind's un-weaving_  
 _Maybe it's best you leave me alone_  
 _A weight is lifted_  
 _On this evening_  
 _I give the final blow_

 _When darkness turns to light_  
 _It ends tonight_  
 _It ends tonight_  
 _Just a little insight will make this right_  
 _It's too late to fight_  
 _It ends tonight_  
 _It ends tonight_

 _Now I'm on my own side_  
 _It's better than being on your side_  
 _It's my fault when you're blind_  
 _It's better that I see it through your eyes_

 _All these thoughts locked inside_  
 _Now you're the first to know_

 _When darkness turns to light_  
 _It ends tonight_  
 _It ends tonight_  
 _Just a little insight will make this right_  
 _It's too late to fight_  
 _It ends tonight_  
 _It ends tonight_

 _When darkness turns to light_  
 _It ends tonight_  
 _It ends tonight_  
 _Just a little insight will make this right_  
 _It's too late to fight_  
 _It ends tonight_  
 _It ends tonight_

Finally the last song they performed;

 _Everybody loves the things you do_  
 _From the way you talk_  
 _To the way you move_  
 _Everybody here is watching you_  
 _Cause you feel like home_  
 _You're like a dream come true_  
 _But if by chance you're here alone_  
 _Can I have a moment_  
 _Before I go?_  
 _Cause I've been by myself all night long_  
 _Hoping you're someone_  
 _I used to know_  
 _You look like a movie_  
 _You sound like a song_  
 _My God, this reminds me_  
 _Of when we were young_  
 _Let me photograph you in this light_  
 _In case it is the last time_  
 _That we might be exactly like we were_  
 _Before we realized_  
 _We were sad of getting old_  
 _It made us restless_  
 _It was just like a movie_  
 _It was just like a song_  
 _I was so scared to face my fears_  
 _Cause nobody told me that you'd be here_  
 _And I swore you moved overseas_  
 _That's what you said, when you left me_  
 _You still look like a movie_  
 _You still sound like a song_  
 _My God, this reminds me_  
 _Of when we were young_  
 _Let me photograph you in this light_  
 _In case it is the last time_  
 _That we might be exactly like we were_  
 _Before we realized_  
 _We were sad of getting old_  
 _It made us restless_  
 _It was just like a movie_  
 _It was just like a song_

 _When we were young_  
 _When we were young_  
 _When we were young_  
 _When we were young_

 _It's hard to win me back_  
 _Everything just takes me back_  
 _To when you were there_  
 _To when you were there_  
 _And a part of me keeps holding on_  
 _Just in case it hasn't gone_  
 _I guess I still care_  
 _Do you still care?_

 _It was just like a movie_  
 _It was just like a song_  
 _My God, this reminds me_  
 _Of when we were young_

 _When we were young_  
 _When we were young_  
 _When we were young_  
 _When we were young_

 _Let me photograph you in this light_  
 _In case it is the last time_  
 _That we might be exactly like we were_  
 _Before we realized We were sad of getting old_  
 _It made us restless_  
 _I'm so mad I'm getting old_  
 _It makes me reckless_  
 _It was just like a movie_  
 _It was just like a song_  
 _When we were young_

Once they finished playing the crowd instantly applauds for them. Jess taps Charlotte on the shoulder. "What did you think?"

"They sounded really good. I'm impressed."

"Do you want to go see Dave backstage?"

"Sure," Charlotte goes up to Tristan and Michelle. "Jess and I are going backstage to see Dave. Do you want come with?" She asks.

"I haven't seen Dave in so long. It would be nice to see a familiar face." Michelle says.

"How do you know Dave anyway?" Tristan asks curious.

"Dave used to live in Stars Hollow and he was good friends with Rory, Michelle and I. He was dating Lane just before he left for California. I don't know if he kept in touch with her." Charlotte explained.

A few minutes later the group were being by Jess to head backstage. He knew security here so they were able to get by without any issues. Once they got passed security, the group were sent down the hallway until they entered the guest room. Jess knocked on the door and a few seconds later the door opened with Dave on the other side with his bandmates.

Dave noticed them as they were entering the room. "Hey guys, long time no see."

"You were great out there!" Michelle gushed with support.

"Thanks, Michelle." Dave hugged her and Charlotte. He turned to Jess, "Thanks for showing up man. I was kinda nervous out there and I thought I was gonna mess up"

"You were cool." Jess simply said.

"Dave these are Charlotte's friends Sienna and Ethan. The guy still standing at the door is Charlotte's boyfriend Tristan." Jess said introducing them to Dave.

"Hey nice to meet you guys. Thanks for coming out to show support." Dave said just as the door was being knocked on. He opens the door and to everyone's surprise it is Austin.

"Hey Austin what's up?" Dave greeted.

"The label was pretty happy with the turnout for your showcase. If you keep this up you might go on tour earlier than expected." Austin said to Dave before noticing everyone else. "Hey guys how's it going?"

"Austin what are you doing here?" Michelle asks.

"Well Dave over here is the newest signee to the label I work for. So I am one of the people who make sure he is obligating his contract." He turns to Charlotte and Tristan. "How are you feeling?"

"I am fine, thanks for asking." Charlotte says feeling Tristan squeeze her hand. She had forgotten Austin was there when she had her breakdown. With all that was going on lately he was the furthest thing from her mind.

"How do you guys know Austin?" Dave asked confused.

"He's our neighbor." Michelle answers.

"Well we have a busy day tomorrow. You have interviews all day and you need to be prepared. So lets get out of here and get some sleep." Austin said before glancing back at the group. "I'll see you guys around."

(Time Skip)

Charlotte and Tristan were sitting on the roof of her apartment building. Jess and Michelle had already went to bed since they had work in the morning. They had all went out to dinner after the club and had a good time.

"It was nice seeing Dave again." Charlotte said.

"Yeah it was nice." Tristan replied weakly

Charlotte looked over at Tristan as he was gazing out at the New York skyline. "Is something bothering you?"

"I'm just happy to be here with you." He says trying to change the subject.

"You know what our problem in our relationship is?" She asked getting a shrug from him. "Communication. We never spoke about our problems until we exploded on each other. In order for us to work, we need to tell each other when we have an issue."

Tristan continued to look at the skyline before releasing a harsh sigh. "I have a question to ask you but I don't know how to ask it without being an ass."

"I will try to receive it before lashing out." She said taking his hand in hers. She rubbed her thumb over his knuckles and waited.

"Is there something going on between you and Austin?" Tristan asks turning his head to stare at Charlotte.

"No." She said quickly.

"Are you not telling me something?"

"I'm going to be honest with you and I need for you to listen and not get angry," She starts getting a nod to continue. "The day after we aired somethings out, Michelle, Sienna, Ethan and I went to Austin's party at his apartment. Austin and I got to talking and then I told him I was leaving to go and see Mom. When I got to the door he stopped me to ask me out. I said I would think about it. I never gave him an answer and I'm glad I didn't."

Tristan looked into her eyes and could tell she was being honest with him. Charlotte was never the type to play with people's feelings when it came to relationships. It was one of the things he admired most about her.

"So where do you stand with him?"

"At the moment we are nothing more than neighbors. I chose to be with you and I am happy with the choice I made." Charlotte said leaning her head on his shoulder.

"I'm glad we talked this out, cause this was bothering me."

"What brought this on?"

"It was something your mother said to me." He added making her take her head off of his shoulder.

"What exactly did she say to you?"

"Something along the lines I might have competition when it comes to Austin."

"Well the next time something is bothering you, tell me so it doesn't fester and make you go crazy." Charlotte says.

"I'll try." Tristan agrees pulling her into his arms.

A couple minutes later Charlotte starts to fall asleep. Tristan watches as his girlfriend as she sleeps. He was glad that they cleared some of his doubts but something in the back of his mind telling him that things between Austin and Charlotte were only beginning. He knew he could trust Charlotte but he didn't know Austin that well. Only time could tell how far things would go.

Tristan picked Charlotte up into his arms. He tried not to jostle her while she was sleeping. They had to get up early if they were going to the Yale-Harvard game tomorrow. Tristan promised his Grandfather he would bring Charlotte to the game. He didn't know what was gonna happen tomorrow, with them meeting the Gilmore's. All he knew was that he was happy with Charlotte in his arms.

*Like I told in the last Chapter, The title of next Chapter will be "Ted Koppel's Big Night Out"

*Charlotte and Rory have a huge blowup at each other because of Jess.

*Emily and Charlotte also have a confrontation.

*The Song(s) are as follow:

 _"The Reason" by Hoobastank_

 _"It Ends Tonight" by The All-American Rejects_

 _"When We Were Young (Cover)" by Ryan Dolan_

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	12. Ted Koppel's Big Night Out

**THE COPYRIGHTS OF THIS SHOW BELONG TO AMY SHERMAN-PALLADINO & WARNER BROTHERS. ALL I OWN IS THE PLOT AND THE ORIGINAL CHARACTERS**

The Life & Times of Charlotte Gilmore Chapter 11: Ted Koppel's Big Night Out

Charlotte was in her kitchen eating breakfast with Jess and Michelle. Tristan had left an hour ago to get his things before they got on the road. She was a little hesitant to be around her Grandparents, mainly Emily.

"What's with the sourpuss face?" Michelle asked looking at her friend like she sucked on a lemon.

"Emily Gilmore." Charlotte replied getting understanding looks from her friends.

"I'd have that face as well" Jess added eating his bacon.

"I already have enough on my mind with work and school. I really don't have time to deal with Emily Gilmore and all her opinions on how my life should be."

"Well you cant avoid her forever and maybe you two will bond today," Michelle offered only to get disbelieving looks from Charlotte and Jess. "Who am I kidding she is going to have something snide to say about how you look."

"Look who cares what she thinks. Just be yourself and make jokes with your mom to get under her skin." Jess said taking his and the girls plates to the sink.

"Thanks Jess." Charlotte said getting a smirk in return.

Charlotte gets up and goes in her room to change her clothes. She had laid out her clothes earlier before she ate breakfast. She was going to wear her black sweater dress, dark blue jeans and her low ankle boots. She had curled her hair earlier and was going to put a beanie over it. Twenty minutes later she came out of her room dressed and her purse on her wrist.

"You look comfortable." Michelle noted from the sofa.

"I wanted something easy to move around in," Charlotte looked around the room and noticed Jess wasn't in the apartment. "Where's Jess?"

"He got called into work early. He said to tell you good luck with Gilmore reunion." Michelle said changing the channel.

"So what are your plans today?" Charlotte asked joining her friend on the sofa.

"I have to be at the gallery later tonight for the auction. Quinn is going to meet me there." Michelle said.

Michelle and Quinn had been going out since they met at Austin's party a month ago. Charlotte had yet to meet him. He seemed like a nice guy from the way Michelle smiles at the mention of his name.

Soon she heard her cell phone ringing breaking Charlotte out of her thoughts. She opened her purse and saw it was Tristan. She answered quickly getting a head shake from her best friend.

"Are you downstairs?" Charlotte asked.

"I am parked out front and can you hurry up" Tristan said hanging up abruptly.

Charlotte looked down at her phone and was confused. She wondered why he had an attitude and hung up on her so quickly.

"I will see you later tonight." Charlotte said hugging her friend.

"Good luck" Michelle called out as Charlotte closed the door behind herself.

(Time Skip)

As soon as Charlotte got in the car Tristan pulled off and they were on the highway into Connecticut. The entire ride Tristan was silent but Charlotte could hear and see his fingers gripping his steering wheel tightly. Charlotte turns in her seat and faces her boyfriend.

"OK what is with the attitude? Ever since you called me to come down you have been angry. Talk to me Tristan." Charlotte demands of her boyfriend.

"Before I came to see you my dad called", Tristan started to say before Charlotte cut him off.

"You don't even have to finish that. I know how your father treats you. I was hoping you would talk to me about it before lashing out on me." Charlotte said seeing the guilt on his face.

"I'm sorry." He said sincerely.

"I get it and I am about to go through the same thing with Emily later on."

"No you're not, Char." Tristan took his right hand off the steering wheel and took her left hand. "As long as we have each other we can get through whatever bullshit comes our way. We can't let anyone get in between us like last time."

"Don't remind me."

"So lets try to enjoy this afternoon and not let negative drama get in the way."

"Its easier said than done. But I will try."

"That's all I ask."

After a few moments of silence Charlotte spoke once more, "What were you talking about with your father?"

Tristan glanced at her quickly before giving the road his entire attention. "We were discussing my work ethic and personal life."

"Such as?" Charlotte probed.

"I cant speak about work because of confidential reasons but we also spoke about you."

"What could he say that made you pissed that you took your anger out on me."

"He said something along the lines that our relationship is not the same it was two years ago. That you are seeing someone besides me and I kinda snapped at him.

"And the seed of doubt was planted by the Jackass."

"It made me think of you and Austin and then all these thoughts came rushing in."

"I thought we talked about this. There is nothing going on between Austin and myself. He showed how he treats girls and I don't want to be in a relationship like that. I don't want to be questioning myself when it comes to trusting the person I am with. If that's the case then I need to be single." Charlotte ranted.

"Are you saying we need to break up?" Tristan asked with a quiet fear.

"No, what I am saying is that I need to be able to trust who I am dating."

Tristan smirked and squeezed her hand lightly. "Now that we have that all cleared up.."

"Shut up and get us to Yale already." Charlotte jokingly ordered.

"As you wish" Tristan said putting more pressure on the pedal and they sped faster.

(Time Skip)

After two hours on the highway, Tristan and Charlotte reached Yale University. Being here brought up a lot of bad feelings for Charlotte. It was constant reminder in everyone's eyes that Rory was special and Charlotte was the extra. She seriously wanted this day to be over with.

Tristan parked the car and turned to face his girlfriend and the look on her face was one he hated to see. All the insecurities Charlotte felt were showing clearly on her face.

"Hey you okay?" He asked breaking her train of thoughts.

"Never better." Charlotte assured him. "Come on lets go meet your grandfather."

They both got out of the car and started to walk through the campus. Charlotte continued to gaze around as they walked pass students milling about.

Just a couple years ago Lorelai had taken Rory and Charlotte out of Stars Hollow after she decided not to marry Max Medina. They had somehow ended up going on a tour of Harvard and Rory had fit in of course. In that moment Charlotte knew no matter what she accomplished it would always be overshadowed by Rory's achievements. She knew her sister wasn't doing it on purpose but it still hurt.

The couple soon saw Tristan's grandfather Janlen Dugray, sitting on a bench talking to a young man. As they got closer the younger man looked at them and Janlen turned to see what had captured his attention.

"Tristan my boy." Janlen greeted as he stood to hug his grandson,

"Hi Grandfather" Tristan said in return.

As the Dugray men hugged Charlotte was happy that someone in Tristan's family was supporting him. Janlen was Tristan's inspiration to be a better person. Janlen then pulled away from his grandson and noticed Charlotte standing beside them.

"Charlotte, my dear you look wonderful. Tristan told me about you working for Ursula Underwood. I am most excited for your future endeavors." Janlen said making Charlotte blush in embarrassment.

"Thank You Janlen." Charlotte gushed.

"I hope we haven't made you wait long Grandfather." Tristan said as they all sat down on the bench.

"Not at all." He glanced at the young man beside him. "I was just speaking to this young man right here."

"I'm Marty it's nice to meet you both." Marty then turned to Janlen. "Mr. Dugray it was nice to meet you as well but I have something important to finish. Hopefully I will see you again, goodbye" Marty aid walking away from them.

"So who else are we waiting for Janlen?" Charlotte asked the older man.

"I was actually invited to join your grandparents Emily and Richard for their BBQ they are having on the other side of the campus. I know you don't have the best relationship with them but we don't have to join them."

"Its fine. Mom and Rory are there and I told them I would stop by and see them."

"Splendid." Janlen said getting up from the bench.

"Granddad have you spoken to dad."

"I did and frankly i don't think you should take anything he says with a grain of salt. Charlotte is a good girl and you'd be lucky to someday have her as your wife. You guys have something and you shouldn't let outside voices disturb it. Now I love my son but he is an idiot," Janlen said getting Charlotte and Tristan to laugh. "Now come along we don't want to make Emily have a fit."

"God forbid Emily wouldn't have a fit" Charlotte remarks.

"You may not like her but she is still your Grandmother." Janlen chides.

"Enough talk lets go and I am hungry." Tristan adds as they walk away from the bench.

(Time Skip)

Soon Charlotte and the Dugrays reached the site where the Elder Gilmore were having there BBQ. When they got there Charlotte tried to relax herself as they walked closer towards the BBQ. She was like her mother in that aspect, where she had to calm herself just to be in Emily's presence.

"Janlen, I was wondering when you would arrive," Emily says briefly before noticing Charlotte and Tristan beside him.

"Hello Emily" Tristan greeted.

"Tristan" Emily said dryly while gazing at her wayward granddaughter. "Charlotte I wasn't expecting you. I would never dream to see you in a place such as Yale." She digged.

"Well my boyfriend invited me and I couldn't turn down a day with him." Charlotte retorted. "I also spoke to Rory and mom earlier, and I promised them I would come to see them. I hope that's not a problem?"

"No not at all. It would have been nice if you had called ahead." Emily sniped just as Lorelai, Rory, and Richard walked over to them.

"Hello Charlotte"

"Hi Grandpa" She replied politely, not caring for the glare Emily sent her way.

"Charlotte" Rory said hugging her sister. "I heard about Sarah Jessica Parker saying your name on the red carpet."

"I know me and Sierra are still in shock. On top of that we are in the finishing stages of the expo and the gala. I am really enjoying working at Underwood designs. So enough about me, tell me what's going on with you."

"Nothing much"

"She's being vague. She went on a date the other week." Lorelai added ignoring the looks she got from her mother and Roy.

"So do you think there is going to be a second date in the near future?" Charlotte asked her sister curiously as they sat down with their mother.

"I don't know. I am not ready to date to be honest after what Jess put me through. I've been thinking about him and I miss him. But I am not ready to forgive him until we speak." Rory confessed.

"Honestly Rory what do you see in that hoodlum?" Emily asked with disdain.

"Grandma you might not like Jess but he is the only guy that understands me personally. He doesn't belittle my success or things I want. He wants me to be the best at whatever I want. He has personal issues within himself that he needs to work on." Rory explained her to grandmother.

"You can do so much better. There must be plenty of boys from good families that would be suitable for you to date. Even Charlotte is dating a boy from a respectable family." Emily said.

"That is the nicest backwards comment you have ever said about me" Charlotte said.

"Lorelai" Emily reprimanded.

"I didn't even say anything this time." Lorelai exclaimed.

"Exactly Lorelai." Emily said walking over to her catering staff.

"That woman is an enigma." Charlotte said as Tristan brought her a plate of food.

"Here's some food." Tristan said sitting next to her.

"How are things with the two of you?" Lorelai asked.

"Well we are boyfriend and girlfriend again. I asked her out after this club we went to with Jess." Tristan said not noticing his girlfriend wincing.

"Jess?" Rory asked confused.

"Yeah, Charlotte introduced us at her apartment." Tristan said noticing the glare his girlfriend was giving him.

Lorelai knew it was about to go down between her daughters. "Tristan could you give them a moment. They need to work things out and it might get ugly."

"Sure" Tristan said leaving the three of them alone.

"How long?" Rory quietly asked once Tristan was out hearing range.

"Since I moved to New York. I ran into him on my first day of school and we've kept in touch. Most recently he's been living with me and Michelle." Charlotte said.

"You've been in contact with him the entire time and you never told me. For the longest time I thought he was in California but he's been in New York with you" Rory accused in a hurt tone.

"Rory." Charlotte started to say before Rory cut her off.

"You of all people should know what I've been through since he left. He was to coward to tell me he couldn't graduate. That is what he does when things get too hard. He runs away and nothing gets solved. I hate the fact that I still love him and he hurt me. What makes it worse is that he is living with you and can't or won't even call me to say sorry."

"Sweets" Lorelai said pulling her daughter in.

Charlotte stood up and joined her mother and sister in the hug. Once all three pulled away, Charlotte grabbed Rory's hand.

"Rory you know how jess is when it comes to emotions. He's like Luke in that aspect. They both have the emotional range of teaspoons." She says making her mom and sister laugh with her. "The reason Jess is living with me is because his apartment caught on fire and I was the only friend he could call. Jess is one of my best friends and he needed me. You can be mad at me all you want but I don't abandon friends."

"Just let me know when he is ready to talk." Rory said walking towards her grandparents.

Lorelai pulled Charlotte back into her arms, "I know it was hard telling your sister all that." Lorelai said walking to join the rest of the Gilmore's.

"I just wish she wouldn't make it about her." Charlotte remarked as Tristan came back towards her.

"You might want to go over there," He said pointing towards the Elder Gilmore.

"What's going on, babe?" Charlotte asked.

"Apparently some woman named Pennilyn Lott came over and asked your Grandfather about Lorelai's inn."

Charlotte smirked and said "Really!?"

"You're evil" Tristan remarked to his girlfriend.

"Sweetie we've barely scratched the surface of how evil I am. Never forget who my mother and grandmother are. Now let's go join the festivities so we can have something to talk about on the drive home." Charlotte says leading her boyfriend back to the BBQ.

As they got closer they could see Emily yelling at Richard. Emily's face was getting redder as she spoke. "You've met with her once a year since we've been married. The woman your mother wanted you to marry. Do you know how that makes me feel, Richard?"

"Emily." Richard says seeing the hurt in wife's eyes.

"I can't even look at you." Emily said walking away from them all.

With Emily walking out of sight the awkwardness in the air becomes stifling. Lorelai attempts to make a joke, "So how about football?"

She gains several weird looks for that comment.

(Time Skip)

After the fiasco at the game yesterday, Charlotte decided she needed to unwind. Being around her family brought out the negative more so, then usual. Charlotte was home alone for the first time, Jess and Michelle were at work. She was sitting at the table in her living room going over some last-minute plans for the expo. It was in a couple of days and she was trying not to stress about it.

Charlotte heard keys opening the front door and it was Jess walking in. He looked exhausted as he walked further into the apartment.

"How was work?"

"A fight happened in the bar. Police were everywhere and they let me leave early." Jess said tiredly as he laid on the couch with his eyes closed. "What are you doing?"

"Going over the plans for the expo." She replied putting down the pencil in her hand. "I got to talk to you about something."

Jess opened his eyes giving her his complete attention. Charlotte took a deep breath before speaking, "Rory knows that you are in New York and that you are living with me."

Jess sat up on the couch and rubbed his face with his hands. "How did she find out I was here?"

"That would-be Tristan's fault. He mentioned when we went out to go see Dave preform." Charlotte explained.

"How angry was she?" He asked.

"I'm not gonna lie, she was more hurt than angry. She feels like you ran away because you couldn't face her. Then she turned it on me and said I was just as bad for defending you."

"Charlotte, I never meant to come in between you and Rory."

"I know that Jess, and so does Rory. She's hurt because she still loves you and you never truly broke up. I need for you to finally fight for your relationship. Rory could have anyone but she wants you. Are you really going to let some douche at Yale get my sister? The only girl who has seen past the broken image you display."

"She could do so much better. Seriously what could I offer a girl like her? She is intelligent and has a future. What do I have that she wants?" Jess said with doubt in his voice.

Charlotte stands up and joins Jess on the couch and pulls him into a hug. "The fact that you know and acknowledge that says a lot. You know what Rory's capable of and yet she still wants you in her life. Are you really afraid of letting her in that you would sabotage your one true moment of happiness?"

"I need time." Jess simply says.

"How much longer are you going to wait. You've been miserable for months and its getting pathetic."

"Jeez, I get it."

"Figure things out sooner than later or you will lose her." Charlotte said picking up her work and heading into her room, leaving Jess with his emotions and thoughts.

(Time Skip)

The next day Charlotte was steaming clothes inside her office. Sienna was typing something on her computer.

"So how was your weekend at Yale?" Sienna asked.

"Entertaining to say the least," Charlotte replied. "Between Rory finding out about Jess living with me and my grandparents arguing about something that could possibly ruin their marriage. I guess you could say I filled my quota for Gilmore family events."

"Rory found out? How?" Sienna asked enthused.

Charlotte then proceeded to tell Sienna all about what happened at Yale, and her talk with Jess last night.

"Your life is like a rollercoaster and you keep doing loop after loop."

"I'm the one living it and it is a shit show." Charlotte added before putting down the steamer. "I was wondering if you and Ethan wanted to go on a double date with me and Tristan sometime this week?"

"I would have to check with Ethan but that's cool with me."

"Great, now I have to bring these clothes back downstairs before Ursula has my head on a plate." Charlotte said pushing the mobile closet out of the office.

*Drama is about to start in the next chapter between Charlotte and Tristan. An old frenemy comes out to play and things will go down.

*The next chapter will be titled "The Expo Part 1", and it will be up sometime towards the end of August.

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	13. The Expo Part 1

**The Copyrights of this show belong to Amy Sherman-Palladino & Warner Bros. All I own is the Plot and the Original Characters.**

The Life & Times of Charlotte Gilmore Chapter 12: The Expo Part 1

(Present Time)

Charlotte and Sienna was sitting in Ursula's office with Ursula, Harper, Yolanda, and Rafael. They were reading the reviews from last night at the expo. It was a success and Ursula was pleased with the outcome. She glanced at her interns and saw one was excited while the other was wearing a fake smile.

"Charlotte is something wrong?" Ursula asked making everyone give their focus to Charlotte.

"Everything is fine" Charlotte replied quickly still reading the reviews.

"Could all of you excuse us for a moment. I need to have a word with Charlotte. I fell she needs some guidance." Ursula said making everyone leave the room but Charlotte. Once the door was closed Charlotte put down the tablet in front of her.

"You have been in a mood since last night." Ursula said pouring herself more tea.

"Things in my personal life have me confused for the moment but I won't let it get in the way of my work like before." Charlotte said reminding Ursula of what happened at the Waldorf Astoria.

"I know I seem like a hard ass Charlotte but I do care about my employees. And from your work ethic I see you can go far in this industry. I just don't want you to squander your potential by letting outside influences distract you." Ursula said with a caring voice.

Charlotte could see her boss was actually being genuine towards her, and it made Charlotte finally brake down. She was still dealing with what happened between Tristan and herself, and her dad showing up to the expo.

"How do you have a life outside of work not affect you?" Charlotte asked Ursula who gave her knowing look.

"Boy trouble I should have known," Ursula said.

"I was told something that changed my view on my boyfriend and I don't know how to feel."

"Well of course you don't," Ursula said getting a confused look before she continued. "Charlotte only you can make a decision on whether or not the information you were given is true. Did your boyfriend even deny what was said?"

"That's the thing, he didn't say anything but walk away. It makes it harder for me to understand anything at the moment."

"Charlotte, I have been married and divorced several times. It is never easy to balance your life. All you can do is try to keep things in check. That is a life lesson you need to value and try to up keep." Ursula advised.

"Thank You Ursula" Charlotte said getting up from the chair and walking to the door.

"Charlotte." Ursula called once more. "I am always here if you need to talk. Now you have work to finish."

(Time Skip)

Charlotte entered her apartment and saw Jess and Michelle setting up the table. She was happy that she had her two best friends living with her. She placed her bag down beside the door and went into the kitchen.

"Hey." She said to her friends.

"How was your day?" Michelle asked hesitantly.

"It was just a work day until my boss told me to manage my life better," Charlotte replied making both her friends stare at her with pity. When she sees the looks on their faces she adds, "Guys I am fine. Yes, Tristan hurt me but I can't let it take over me."

Michelle stopped what she was doing and sat down across from her friend, "Do you not remember the last time you and Tristan broke up?"

"Of course, I do."

"I don't you spiraling out of control like last time. You were lashing out on everyone and things are great for you now. I just need for you to know that you have a lot going for yourself."

"Last time was different, he didn't say anything, and this time he lied." Charlotte said.

"Have you spoken to him since?" Jess asked as he brought the food to the table.

"He's been calling for the last couple of days but I haven't picked up. I honestly have so many questions and I don't know what to say." She said making Jess and Michelle look at each other once more.

"Eventually you are going to have to talk to him. Or he'll show up randomly and piss you off." Jess said.

"I'm not hungry anymore and im exhausted, "Charlotte said getting up from the table. "I will see you guys in the morning.

She heads to the door to get her bookbag and then walk through the living room into her bedroom. She closes her door and hears Michelle and jess's voices through the door.

"I hope she'll be okay. I'm worried about her and I don't want her reverting to that angry person she was a year ago." Michelle says.

"When she is ready to confront Tristan, she will tell us. Until then all we can do is be there for her." Jess said ending their conversation.

Hearing those words come out Jess's mouth just made that night repeatedly appear before her eyes. She wasn't ready to confront him but she still wanted to know where everything went wrong.

 _(Flashback – Yesterday)_

 _Charlotte was watching as the finishing touches to the Expo were being set up. She had been at the gallery all morning regulating everything. She glanced over at Sienna and Yolanda as they were going over the directions for tonight._

 _"Sweets" Charlotte heard her mom's voice. She turned around and saw Lorelai and Sookie coming up to her._

 _"Hi Mom", Charlotte said to her mother as she hugged her. She then did the same to her mom's best friend. "Hi Sookie, I can't thank you guys enough for catering this entire thing."_

 _"We're glad to help," Sookie looked around and stared at Charlotte. "So where do we set up?"_

 _Charlotte led them to the catering station that had been setup the night before. "I hope you can work with this Sookie. I made sure you had enough space to get things done."_

 _"This is fine, I've worked in smaller places. How is everything else?" Sookie asked._

 _"Everything has to be perfect for tonight. We have several magazines and newspapers coming to see the expo so they can get a taste of what the gala event will be like. It's my first big event that determines my career. I'm good under pressure so no biggie." Charlotte tells her mother and Sookie._

 _"As long as you don't stress yourself you'll be fine. So what kind of model will be there?'' Lorelai asks with her mischievous smirk._

 _"They are half your age and I am in a relationship." Charlotte dryly replies to her mother who pouts._

 _"Your no fun." Lorelai adds._

 _Charlotte sees Yolanda beckon her over, "Mom will speak with you guys later. I have to get back to work."_

 _"Ok Sweets, we've got everything covered with the food." Lorelai says as Charlotte walks away from her and Sookie._

 _Once Charlotte reaches Yolanda and sienna she tells them that the caterers are setting up._

 _"Great that is one less thing for us to worry about," Yolanda says with stress in her voice._

 _"What else needs to be done?" Charlotte asked._

 _"The designers are all in the next room fitting the clothes on the models. I need one of you to take photos of the models in the clothes. The other does a head count of the models and the designers. Then we need to put the place cards in the seats surrounding the catwalk. Everything else is being checked over by Rafael." Yolanda says._

 _Charlotte turns to Sienna, "I will do the headcount and you take the photos."_

 _"Fine by me" Sienna says as they both head for the room next door._

 _Sienna opens the door and the girls are both in awe and annoyance. Designers were everywhere running around to put the last touches on their work. Charlotte was impressed with some of the craftsmanship, other outfits made her cringe._

 _"We have a lot of work cut out for us." Sienna remarks in irritation._

 _"Come on, the quicker we get this done the faster we can get away from them." Charlotte adds leading her friend further into the room getting looks from a few people._

 _As they reached the front of the room with the call sheets they both sighed seeing all the paperwork. "Let's get started."_

 _(Time Skip)_

 _After going through hundreds of names Charlotte and Sienna were exhausted. They still had a couple more to do and go and get ready for later tonight. Yolanda had joined them eventually after the runway was setup._

 _"You girls have got a lot done so far. Why don't you guys go and get lunch?" Yolanda suggested._

 _"Do you want anything?" Sienna asked._

 _"Just get me a turkey club." Yolanda replied offhandedly as she continued working. Charlotte and Sienna left Yolanda and headed for the exit. As they were walking Charlotte accidently bumped into a girl._

 _"I'm sorry," Charlotte immediately apologized._

 _"It's fine, I wasn't paying attention to wear I was going." The girl said with polite smile. "I'm Fiona Darden."_

 _"Charlotte Gilmore." Charlotte says and then she notices Sienna still standing next to her. 'this is my friend Sienna Miller."_

 _"Nice to meet you." Sienna said. "Charlotte lets hurry and get lunch. We have more stuff to do before tonight."_

 _"I'm coming" Charlotte says to Sienna before she leaves. "Well it was nice meeting you and I hope to see you later tonight."_

 _(Flashback End)_

(Present time)

Charlotte went into her closet and took her keyboard out. She was tired of feeling this doubt that laid with in herself. Wondering if she was good enough for anyone to love. She began to play the keys. A melody came to her and she began to sing.

 _Perfect, picture one so picture perfect_  
 _As your lies disguised as loving arms_  
 _The future looked so bright, but it was blinding_  
 _Oh, why couldn't see the man behind the charm?_

 _Then we closed the doors and the lights came on_  
 _And I saw the real you_  
 _No, I don't like him_  
 _Don't like how it feels_  
 _I want a new you_

 _It's taking everything in me_  
 _Not to hurt you like you hurt me_  
 _Cause I wanna get you back, but I gotta keep moving_  
 _Boy, I swear you don't know_  
 _It's taking everything in me_

 _Searching, searching, still can't find an answer_  
 _Cause all this wasn't part of the plan_  
 _So now it [?]_  
 _Oh, where do we go from here?_

 _Cause behind closed doors, when the lights are on_  
 _You become the real you_  
 _No, I don't like him_  
 _Don't like how it feels_  
 _I want a new you_

 _It's taking everything in me_  
 _Not to hurt you like you hurt me_  
 _Cause I wanna get you back, but I gotta keep moving_  
 _Boy, I swear you don't know_  
 _It's taking everything in me_

 _Sometimes people hurt you_  
 _That just means they don't deserve you_  
 _And you want to do the same to hurt them back_  
 _But this one's for you know who_  
 _You're the one who looks like a fool_  
 _And there's no greater revenge better than that_

 _But it's still taking everything in me_  
 _Not to hurt you like you hurt me_  
 _And I just wanna get you back I gotta keep moving_  
 _Swear you just don't know_  
 _It's taking everything in me_

 _Everything in me_  
 _Everything in me_  
 _Everything_  
 _Everything in me_  
 _Everything_  
 _Not to do to you_  
 _What you did to me_

As Charlotte sung the last verse she saw the rain drops outside her window. She felt much better but she could feel some of the resentment towards Tristan sitting in her chest. Charlotte decided in that moment, she was done wallowing. She placed the keyboard on her bed as she went into her purse and pulled out her phone. She saw another ten missed calls from him. She hit redial and waited for him to pick up.

"Charlotte." Tristan answered frantically.

"When were you going to tell me, you were once engaged?" She asked softly into the phone as tears fell down her face.

"I don't want to have this conversation over the phone. We need to see each other face to face. Can we do that?" Tristan asked hesitantly.

"I'm not so sure that's a good idea. I'm afraid of what I would do to you if I see your face." Charlotte warned the boy.

"I need to see you."

"I have always been upfront about everything when it came towards me. Until you can give a me a legitimate reason for not saying you were once engaged. I don't think we can be around each other. I think we need space."

Once those words came out of Charlotte's mouth it was like time stopped for both of them. A couple of seconds later Tristan finally responded, "When you're ready to talk I am here."

"Will see" Charlotte said hanging up. She stared at her phone for a few momemts before turning off the lights and going to sleep.

(Time Skip)

Charlotte, Sienna, and Michelle were walking down the street with shopping bags. Sienna and Michelle decided that Charlotte needed some retail therapy after her split with Tristan. They had been shopping for several hours and Charlotte was exhausted.

"Thank guys I really needed this today." Charlotte said to her friends as they entered Victoria Secret.

"You were acting like a zombie and Jess needed the apartment for his study group." Michelle said as she was looking at lingerie. "And I needed some new winter clothes especially with what I am planning for all of us."

"What are you talking about?"

"Well you know how me and my dad are working things out between us?"

Charlotte glanced at her friend with a sympathetic look, "You haven't even mentioned it to me. I would have remembered you saying that."

"I could have sworn I did, but anyway," Michelle said continuing. "My dad has decided to let me use the cabin out in Vermont and I'm taking all of us."

"Whose all of us?" Sienna asked as she sniffing perfumes and lotions.

'Obviously you two, Jess, Ethan, Dave and I was thinking Rory and Lane." Michelle said.

"Michelle, I don't think Jess is going to go if Rory comes." Charlotte stated as she headed into the dressing rooms. "They still haven't seen each other since Jess bailed on her last year. They both know that Jess is living with me though"

"This might be the perfect opportunity for them to talk." Michelle called out to Charlotte.

"since it was your idea you have to be the one to tell Jess that your thinking of inviting Rory." Charlotte said making Sienna laugh at the expression of fear on Michelle's face.

"Hopefully he doesn't chew your face off" Sienna added making Charlotte and Michelle laugh.

As Charlotte came out of the dressing room she bumped into someone. When she saw whose face she was staring at, Charlotte's became stone like. It was Tristan's ex fiance.

"Charlotte."

"Fiona"

Fiona fidgeted for a moment before she spoke once more, "Look I know this is awkward for you and I. I just want to clear the air between the two of us if that is possible?"

"What is it you have to say to me?"

"I want to apologize for any problems I caused for you and Tristan. We had a weird engagement to say the least, and for my part I am sorry."

"My problem isn't with you Fiona. Tristan is the one who never told me his situation. I have no issues with you and thank you for your apologies but it isn't wanted nor needed." Charlotte says to the girl.

"I understand your still hurt," Fiona said as she pulled a card out her purse. "When you're ready to talk here is my number."

Charlotte took the card from Fiona and glanced at it, she ten nodded towards Fiona who smiled apologetically before walking away.

"Who was that?" Michelle asked as she and Sienna walked towards there friend.

"That would-be Tristan's ex-fiancé. She wanted to apologize for her part in all this. My anger isn't towards her, she is innocent in all this. Tristan lied to me, the guy I am supposed to be in a relationship with." Charlotte explained.

"How about we go and see a movie?" Sienna suggested.

Charlotte shook her head and walked away from her friends. She could hear their footsteps behind her as they rushed to catch up to her.

"Where are you going?" Michelle asked concerned about her friend.

"I need space right now. This helped and I really appreciated you guys trying to help me. But right now, I want to be alone with my thoughts. I'll see you at home" Charlotte said leaving her friends alone on the sidewalk.

 _(Flashback – Yesterday Night)_

 _Once she had triple checked everything, Charlotte had rushed home a couple of hours ago. The Gallery was set up for the Expo and Ursula was ecstatic. She had praised Charlotte and Sienna for all the planning that was put in to this._

 _She had just finished putting her dress on when she heard a knock at her door. "Come in."_

 _Jess opened her door and said, "Romeo is waiting for you downstairs."_

 _She turned to Jess and smiled, "How do I look?"_

 _Charlotte was wearing an ivory jumper, her matching pearl necklace and earrings, with a nude pair of pumps, and on her bed, was a black clutch to complete the outfit. She put her hair in a bun at the nape of her neck._

 _"You look good."_

 _"What are you doing tonight?" Charlotte asked Jess as she put her lipstick on._

 _"Dave is coming by so were gonna hangout on the roof. Michelle said she is going on a date. You know where I'll be when you get back." Jess told her as he left her to finish putting her make up._

 _As Charlotte finished putting the rest of her make up on, she was thinking about tonight. She had come up with the idea for the expo and Ursula liked it. Now that the Expo was tonight she wanted everything to go off without a hitch. It was her job on the line and she needed it to go right._

 _Charlotte grabbed her clutch and walked out of her bedroom into the living room. She saw Jess writing something in a notebook._

 _"I will see you later tonight. Wish me luck", She said heading for her jacket beside the door._

 _"You don't need any luck." Jess said with his trademark smirk._

 _"Bye Jess" She said closing the door behind her. As she walked down the hallway the door on her right-side opened and Austin came out with a girl and some old man._

 _"Hey Charlotte, you heading out?" Austin asked as he looked her up and down._

 _"Yeah I have a work thing." Charlotte replied heading for the elevator._

 _"Son who is this young lady?" The old man finally spoke up._

 _"Oh, sorry dad", Austin said to the man. "Charlotte this is my father Cliff Matthews and his secretary."_

 _Charlotte turned around and looked at the man. She could see the similarities in his face with Austin's. "It is nice to meet you but if you can excuse me I am running a bit late." Charlotte said pressing the button for the elevator._

 _As she entered the elevator and the doors close she could have sworn she heard Austin's father telling his son he needed a woman like her. She shook her head and thought, 'He almost had one'._

 _(Time Skip)_

 _Charlotte walked out her building and saw her boyfriend looking dapper as usual. He was leaning on his Porsche gazing at her as she got closer towards him. H was wearing a white collared shirt over a nice pair of dark wash jeans._

 _"You look perfect." He admired as she twirled before stopping in front of him._

 _"Thank You," She said with a grin. "You don't look so bad yourself."_

 _She leaned up and gave her boyfriend a kiss. AS she tried to pull away she felt his arm wrap around her waist and pull her close to him. Once her chest is pressing on his abs, she glances and see his normal blues darken with lust._

 _"Why start something like that?" He asked desperately._

 _"Be a good boy and you might be rewarded tonight." She said seductively making him grin appreciatively. "Now we have to be at my school for the Expo."_

 _Tristan opened the door for her and once she sat down he closed her door, ran to his side of the car. Once he got inside the car he took his right hand and grabbed her left hand and squeezed it. He turned on the car and sped down the street._

 _(Flashback End)_

(Present Time)

Charlotte walked inside Mr. Sutherland's music shop. The last time she was hear he offered a piano to her and right now she needed to vent. As she walked further into the store she heard a guitar being strung she saw a guy with his back turned to her. He soon began to sing

 _Gravity is pulling you in_  
 _Cause the earth it won't stop spinning_  
 _It's no surprise_  
 _You found me again_  
 _After all it was the best thing that we ever had_

 _Now sugar, I can see you honey_  
 _Ooouuuu lets not pretend that it's here babe_  
 _The world that we know disappeared long ago_  
 _Cause we just couldn't carry the weight_

 _I know you all, want someone to care_  
 _To find the words when you can not find them yourself_  
 _The things you lost, you'll never get back_  
 _It's too late, you're just gonna drag out the past_

 _Now sugar, can't you see oh honey_  
 _Ooouuuu lets not pretend that it's here babe_  
 _The world that we know disappeared long ago_  
 _Cause we just couldn't carry the weight_

 _This time what are you searching for_  
 _The better days you thought you had before_  
 _So what if you don't see it anymore_  
 _Can you hear what I sayy-_

_Oh yes now sugar, I can see you honey_  
 _Ohh now baby_  
 _Ooouuuu lets not pretend that it's here babe_  
 _The world that we know disappeared long ago_  
 _Cause we just couldn't carry_

 _Ooouuuu lets not pretend that it's here babe_  
 _The world that we know disappeared long ago_  
 _Cause we just couldn't carry the weight_  
 _Just couldn't carry the weight_  
 _Just couldn't carry ohh_  
 _Just couldn't carry ahh_  
 _Just couldn't carry ooouuuu_

Just as the last chord was strung the mystery guy heard clapping from behind him. He saw Charlotte standing behind him with a smile.

"Can I help you?" He questioned rudely.

"Is Mr. Sutherland here?" Charlotte asked him, ignoring his rude demeanor.

"My grandfather is in his office." The guy said turning back to his guitar.

"Nice talking you jerk," Charlotte said under her breath as she headed for the office. She didn't notice the glare that the guy was giving her as she walked pass him. She knocked on the door before entering.

"Come in", Charlotte heard as she opened the door.

Mr. Sutherland looked up from the magazine he was reading and motioned to the chair in front of his desk, "I was wondering when you'd show up again. Have a seat."

"I met your grandson out there. He seems nice enough." She told the man as she sat down.

"Kyle is a little of an asshole but who isnt? Now what brings you by my dear?"

"I'm gonna be using the piano here in your store. I wanted to get away from everyone just for a day. Is that all right with you?" Charlotte said to the old man.

Mr. Sutherland stared at the girl and could see she has something to express, "My store is yours" He told her with a knowing smile.

Charlotte smiled thankfully and stood up from the chair and walked out of the office. She walked around the store until she found the piano she used the last time she was there. She sat down on the bench. She slid her hands across the keys before she began to play

 _I don't know what I've done_  
 _Or if I like what I've begun_  
 _But something told me to run_  
 _And honey, you know me, it's all or none_

_There were sounds in my head_  
 _Little voices whispering_  
 _That I should go and this should end_  
 _Oh, and I found myself listening_

_'Cause I don't know who I am, who I am without you_  
 _All I know is that I should_  
 _And I don't know if I could stand another hand upon you_  
 _All I know is that I should_  
 _'Cause she will love you more than I could_  
 _She who dares to stand where I stood_

_See, I thought love was black and white_  
 _That it was wrong or it was right_  
 _But you aren't leaving without a fight_  
 _And I think, I am just as torn inside_

_'Cause I don't know who I am, who I am without you_  
 _All I know is that I should_  
 _And I don't know if I could stand another hand upon you_  
 _All I know is that I should_  
 _'Cause she will love you more than I could_  
 _She who dares to stand where I stood_

_And I won't be far from where you are if ever you should call_  
 _You meant more to me than any one I, I've ever loved at all_  
 _But you taught me how to trust myself_  
 _And so I say to you, this is what I have to do_

_'Cause I don't know who I am, who I am without you_  
 _All I know is that I should_  
 _And I don't know if I could stand another hand upon you_  
 _All I know is that I should_  
 _'Cause she will love you more than I could_  
 _She who dares to stand where I stood_  
 _She who dares to stand where I stood_

"You were a little off key, but what can you expect with an amateur." Kyle stated.

Charlotte turned to the sullen guy behind her, "I'll take that into consideration. I thought you wanted to be left alone."

"I was trying but your singing distracted me for a moment. I'm not going to lie but you sound okay. I can hear you trying to say something but its stuck." Kyle explained.

Charlotte stood up and faced Kyle, "You remind me of my friend. He has a hard time of letting people in and once he does, he has a hard time of letting them go. I'm Charlotte."

"Kyle."

"I haven't seen you around. You live around here?" She asked curiously.

Kyle leaned against the piano and folded his arms. He gazed at Charlotte for a moment before he spoke, "I just moved to New York a couple of weeks ago. I got in to Juilliard a couple of days ago and I've been trying to settle in. It helps that gramps is around so I am not too lonely."

"It helps to speak about these things." Charlotte added.

In attempt to change the topic of discussion from himself Kyle asks, "What's your story?"

"What do you mean?"

"You were singing that Missy Higgins song. Obviously, something in your life has you questioning yourself. Whether your good or not?" Kyle said as he observed her stance and how she was shifting in discomfort.

Charlotte had barely spoken to this guy and already he could see right through her. It was unnerving that a total stranger could speak with such conviction about her while she was in denial of what to do with herself. She always thought she and Tristan were endgame but, meeting his ex-fiancé put things in perspective. What else did she not know about him? What other secrets was he hiding from her? These were questions she would only get form the source but Charlotte wasn't ready to meet with him.

*The next chapter will be up in early October and it will be the continuation of this chapter "Expo Part 2".

*Kyle Sutherland will be portrayed by Matt Mullins. He and Charlotte will be working together on music in the next couple of chapters. Tristan and Kyle will run into each other and drama will occur.

*I'm already working on the crossover chapter with _"Logan Grey: The Long Lost Brother"_ & _"Reasons"_. It will be up by October – Late November. Work and School will be picking up soon for me. I will try to post regularly.

*The song(s) are as follow:

 _"Everything In Me" by Sevyn Streeter_

 _"Let's Pretend" by 16 Frames_

 _"Where I Stood" by Missy Higgins_

PLEASE FOLLOW. FAVORITE, & REVIEW

CHAZ746


	14. Author Message 1

**Author's Message:**

1\. Hey guys my laptop was being fixed at BestBuy and they ruined it deleting all my notes for the next couple of chapters. Thankfully I have everything saved on USBs & External Hardrives.

2\. I am in the process of buying a new laptop as well so I won't be updating for quite some time. I will try to update something with in the next couple of weeks especially with my work schedule changing.

3\. _"Digimon 02 Redux"_ will be going on hiatus for a total update and reboot.

4\. I was also in the process of starting my own Arrowverse Fanfic. If you have any inputs please inbox me for ideas.

5\. Finally the three-part crossover I've been obsessing about in my mind will be up by late November – early December. I am almost finished with part 2 and 3 but still working out the plot for part 1.

 **Please Follow, Favorite, & Review**

 _"The Life & Times of Charlotte Gilmore"_

 _"When All Is Said & Done"_

 _"Logan Grey: The Long Lost Brother"_

 _"Scion: Agent of S.H.I.E.L.D."_

 _"Reasons"_

 **Until next time,**

 **Chaz746**


	15. The Expo Part 2

**The Copyrights of this show belong to Amy Sherman-Palladino & Warner Bros. All I own is the Plot and the Original Characters.**

The Life & Times of Charlotte Gilmore Chapter 13: The Expo Part 2

It had been a few days since Charlotte had spoken on the phone with Tristan and she felt numb. Her talk with Mr. Sutherland's grandson Kyle made her realize that her doubts. The ones that were plagued with all her insecurities. The issues that she dealt with all her life. If she was ever good enough. These thoughts have been in Charlotte's mind ever since she could remember.

Charlotte was broken out of her thoughts by a knock-on bedroom door. She straightened herself before saying, "Come in"

Her bedroom door was opened by Michelle holding a tray of food. She walked up to Charlotte and placed the tray on Charlotte's lap.

"You didn't eat this morning." Michelle said concerned.

"I haven't been eating lately. I've been so stressed with this Tristan thing that I didn't even finish some of my school work and I have a meeting with Ethan's mom." Charlotte said nibbling on a piece of food from the tray.

"Have you spoken with your mom since that night?" Michelle asked.

Charlotte shook her head, "I called her yesterday but she's going through something with Grandma and I don't want to worry her."

"Don't forget tonight we are all going out for dinner." Michelle reminded as she walked to the door.

"I won't," Charlotte replied eating the sandwich as her friend closed the door.

(Time Skip)

Charlotte was sitting in Olivia Walker's office. It had been a month since she last sat in the office and a lot of things had happened since then. She had been waiting for over five minutes and she was getting a little stir crazy. She soon heard the door opening and turned around and saw Olivia walking in with two cups of coffee.

"I have it on good authority you are a coffee fanatic." Olivia quipped as she handed Charlotte a cup.

"My mother always say she was the bastard child of Folgers." Charlotte jokes as she sips her elixir of life.

Olivia sits down and opens the folder and reads it for moment before looking up to Charlotte's face. "You've done well here up until recently. According to your professors a couple of days ago you've been distracted as of lately. Is there something going on with you?"

"Just teenage problems." Charlottes says.

"What did the guy do?"

"Wow your like a hound with a killer nose." Charlotte adds.

"I grew up with two older sisters. They had the same look that you had and it always leads to boys." Olivia says looking at her watch. "We've got about ten minutes before my next meeting and I need something to keep me from falling asleep."

Charlotte then proceeds to tell her all that is going on. Olivia listens and nods at certain points and waits for Charlotte to finish.

"Well from what you've told me it seems like you need to sit down and talk with him. You're going to stress yourself wondering about the what ifs. Go and talk to the boy, and if you don't like what you hear take the space you need to figure things out."

Charlotte picks up her bag and heads to the door, "Thanks Ms. Walker."

"One more thing Charlotte," Olivia says getting Charlotte's attention. "You have until next Monday to get all the work you missed done. All your professors agreed with my terms. Don't fail now especially since your very gifted."

Charlotte nods and walks out of the office and sees Ethan. He looks up from what he's doing.

"How did the talk with my mom go?"

"She gave me the same advice everyone else has given me. Go and talk to Tristan or keep stressing."

Ethan sees the look on her face and asks, "So, what are you going to do?"

"I haven't decided yet. On another note, you coming to dinner tonight?"

"Yeah, Michelle texted me the time and address. What are you going to do right now?"

"I'm going to class and then meet Sienna at Underwood's." Charlotte says hugging him before walking away from him. "I'll call you later"

"Okay," Ethan says in return watching her leave for her next class.

(Time Skip)

Michelle, Jess, and Sienna are sitting around a table outside of a cafe. They had all decided to meet to talk about Charlotte and the way she has been acting lately.

"She is kind of spiraling out of control." Sienna says. "She's been forgetting stuff at photoshoots and I've been picking up the slack. It's beginning to get too much now and something needs to be done."

"She hasn't been eating either." Michelle adds getting wary looks from Jess.

"That's why I called for reinforcements," Jess says getting Michelle and Sienna's attention as he points to Lorelai and Rory.

"You actually called Rory?" Michelle says shocked.

"Charlotte's important to me and that means even putting aside my issues with Rory." Jess explains as the Gilmore girls sit down with the three of them.

"I'm just as surprised as you Michelle." Lorelai adds. "When Rory told me, Jess called because Charlotte was going through things I didn't believe it. Then I remember which daughter I was dealing with. Get me up to speed on things."

"Weren't you at the expo?" Jess asked.

"I was there in the morning when things were being setup. I left an hour before everything started. Charlotte was supposed to call me that night to tell me how things went but she never did." Lorelai answered seeing the looks on their faces. "What happened that night?"

"Well things went really bad for her." Michelle said.

"How bad?"

"She found out that Tristan was previously engaged. On top of that she didn't find out from him." Sienna explained.

"Who did she find this out from?" Rory asked.

"From the ex-fiancé." Jess answered as Lorelai and Rory winced. "Since then she is slowly shutting down like when he left."

"I'm glad you guys called us but, where is she?" Lorelai inquired.

"That's the thing after class she said she had to do something. She said she would meet us after." Michelle said.

(Time skip)

Charlotte had finished school earlier and was going to get answers one way or another. She was tired of doubting herself and that need to stop. She was now driving to Tristan's apartment to finally air things out and put everything behind them. It was raining in the streets of New York and it only cemented how Charlotte was feeling.

When she stopped at a red light she turned on the radio exactly as a DJ announced the next song. She heard the beginning of a strum of a guitar as the song started playing,

 _Incompatible, it don't matter though_  
 _'cos someone's bound to hear my cry_  
 _Speak out if you do_  
 _You're not easy to find_

 _Is it possible Mr. Loveable_  
 _Is already in my life?_  
 _Right in front of me_  
 _Or maybe you're in disguise_

 _Who doesn't long for someone to hold_  
 _Who knows how to love you without being told_  
 _Somebody tell me why I'm on my own_  
 _If there's a soulmate for everyone_

 _Here we are again, circles never end_  
 _How do I find the perfect fit_  
 _There's enough for everyone_  
 _But I'm still waiting in line_

 _Who doesn't long for someone to hold_  
 _Who knows how to love you without being told_  
 _Somebody tell me why I'm on my own_  
 _If there's a soulmate for everyone_

 _If there's a soulmate for everyone_

 _Most relationships seem so transitory_  
 _They're all good but not the permanent one_

 _Who doesn't long for someone to hold_  
 _Who knows how to love you without being told_  
 _Somebody tell me why I'm on my own_  
 _If there's a soulmate for everyone_

 _Who doesn't long for someone to hold_  
 _Who knows how to love you without being told_  
 _Somebody tell me why I'm on my own_  
 _If there's a soulmate for everyone_  
 _If there's a soulmate for everyone_

Tears were streaming down Charlotte's face as the song ended. She looked out the window and saw she was in front of Tristan's apartment. She pulled a mirror out of the glove compartment so she could straighten her make up. Charlotte didn't want Tristan to know she was crying. Once she felt she looked better she got out of the car and walked into the building. She walked to the elevator and saw several people stepping on.

A few minutes later Charlotte was in front of Tristan's door. She knocked on the door and heard a shuffling sound on the other side of the door. The door was swung open with quickness and a haggard looking Tristan was what greeted her. The look on his face when he saw her was one of hurt.

"We need to talk." Charlotte said softly.

"I agree," Tristan added as he moved away from the door. "Come in. Do you want coffee?"

"Yeah, that would be nice." Charlotte replied siting down in his living room. Charlotte could see his apartment was a mess and knew he was feeling exactly how she was feeling in some aspect. Tristan soon came back with a mug of coffee.

"Here." He said handing her the cup. "Sorry about the mess I've been meaning to clean up a bit."

"It fine," Charlotte said staring at her boyfriend. She could see the stubble on his face and the black rings around his eyes.

"How've you been?" Tristan asked as Charlotte continued to stare at him.

"I've been trying to figure out how that night became a disaster. I want to know why you didn't tell me you were engaged. Did you think I would never find out about in some shape or form?"

Tristan stood up and sat down next to Charlotte, "No I was going to tell you on my own terms. That relationship wasn't of my own doing."

Charlotte had briefly remembered the words Fiona had spoken to her when they ran into each other. "What exactly do you mean?"

"After I had graduated from Military school, I was really unhappy. I was in a place in my life where I felt alone. When I returned to Connecticut to see my family all I thought about was seeing you. I knew the way we had ended things wasn't great."

"You think." Charlotte quipped getting a smirk from Tristan.

"As I was saying, I wasn't great and I wanted to see you but Rory said you were finally in a good place after I left you abruptly. Around that time, I met Fiona and she was different. My father liked her a lot especially because of who her family was. She understood the whole family obligation thing. She also knew I was still in love with you."

"If she knew you were still in love with me then, why did you both choose to get engaged?" Charlotte asked.

"We had no choice seeing as both out parents wanted us to be together to unite our families. Fiona and I stayed engaged for about a year until we both called it quits. Seeing as we both loved someone else."

Charlotte stood up from the couch and walked towards the window by the wall and saw the rain was coming down harder. She soon heard his footsteps behind her and felt when he put his hand on her shoulder.

"I am sorry for not saying anything."

Charlotte turned to face him and he saw tears on her face, "Is there anything else I should know?"

"I'm really sorry you had to find out like this. I was going to tell you on my own terms." Tristan said remorsefully.

Charlotte was angry at him for not telling her this. But she couldn't really be upset with him because they weren't together at the time. It all just confused her to say the least.

"I need to think about things. I know I want to be with you but I am still angry and I don't want to say anything until I calm down completely."

Tristan scratched his head as he said, "I get it just don't leave me waiting for too long." Tristan then pulled her into a hug and kissed her forehead. She could feel his stubble scratching her forehead as she pulled away.

"Now that we've spoken you need to go and shave."

"Why?"

"All though you look hot with it, I like my man clean shaven." She said walking to the door.

"I'm still your man?" Tristan asked with hope.

"I can't make a decision right now but you're still in the running." Charlotte said opening the door and leaving him standing alone in the apartment.

(Time Skip)

After finally speaking with Tristan, Charlotte felt a weight drop off her shoulder. All she knew was that she wanted a bacon cheeseburger with the works. She parked the car in front of the café she was supposed to meet her friends.

As she approached the table Charlotte saw Michelle, Jess, and Sienna sitting and talking. She sat down beside Jess, "I am starving, can one of you order me a bacon cheeseburger."

Michelle seeing her friend was in a good mood, "You look chipper."

"I just came from speaking with Tristan." Charlotte said as she saw two extra chairs at the table. "Who are those seats for?"

"Us," Charlotte heard making her turn around in her seat seeing her mother and sister. "You've been dodging my calls missy."

"Mom what are you and Rory doing here?" Charlotte asked staring at her friends who weren't staring at her.

"Your friends were worried about you. You also didn't even call me to tell me about how the event went." Lorelai said.

"Well the event got rave reviews while my life went to shit." Charlotte said as a waiter came by. "Can I have a Bacon Cheeseburger with the works and some fries and onion rings on the side?"

"Anything else?"

"A huge glass of lemonade." She replied.

"We will also have that." Rory added as she pointed to herself and their mother.

Once the waiter left Lorelai gave Charlotte her crazy look, "Now tell Mommy all about that night and don't leave out any of the details."

Charlotte sighed as she regaled them of what happened that night.

 _(Flashback Begins – The night of the Expo)_

 _Charlotte and Tristan walked into the FIT museum and saw people mingling about. Charlotte grasped her boyfriend's hand and leads him further into the party. A couple of waiters pass by with h'orderves and as they walk towards the catwalk._

 _Charlotte sees Sienna with a headset on her head as she speaks with someone. She taps Tristan on his shoulder getting his attention._

 _"I see Sienna over there and I have to go backstage to help coordinate the show. Find a seat and I will see you after." Charlotte said._

 _Tristan kissed her cheek and said, "Go break a leg."_

 _She smiled and walked away from her boyfriend. She walked pass a waiter and bumped into someone. She noticed it was man who from the looks of his clothes was important._

 _"I'm sorry." Charlotte apologized. "I didn't see you there."_

 _"It was my fault. Let me get you a drink." The man offered._

 _"Can't I am working right now." Charlotte replied with a shake of her head. "I didn't get your name."_

 _"William Underwood."_

 _Charlotte's eyes widened in acknowledgement. The man in front of her was her boss's son and one of the richest men in Manhattan. He was recently on the Forbes list for selling one of his tech companies for close to half a billion dollars._

 _"I am really sorry for bumping into you Mr. Underwood." Charlotte said apologizing once more as William Underwood chuckled._

 _"Pleas just call me Billy. Like I said before it was my fault." Billy said with a grin._

 _Charlotte glanced over to Sienna and saw her waving for her to come backstage. "If you will excuse me."_

 _"Go on right ahead Charlotte," He said with a smirk._

 _Charlotte paused and said, "How do you know my name?"_

 _"You didn't think I wouldn't know who you are?" He asked as she shook her head. "My mother speaks highly of you especially since this was all your idea. Have a good night Charlotte and good luck with everything."_

 _William Underwood walked away from Charlotte with grin. Charlotte put on a smile and headed towards Sienna. She stepped on the stage and headed for the back. She saw her friend with Yolanda yelling at the designers to get their last-minute alterations done._

 _"How is everything going so far?" She asked as Yolanda dealt with one of the designers._

 _Sienna looked up from the clipboard and grimaced, "Everything is almost done. Sookie has all the food ready to be served out front. The lighting is done thankfully and all that's left is getting the designers finished in the next thirty minutes."_

 _"Sienna calm down." Charlotte ordered. "I'll deal with the designers while you make sure any last-minute details are done."_

 _"Thanks Char," Sienna sighed as she appraised Charlotte's jumpsuit. "You look stunning."_

 _Charlotte looked down at what she was wearing, "Can you believe me and mom made this?"_

 _"It's beautiful Charlotte." Sienna complimented._

 _Before Charlotte could respond Ursula arrived with Sarah Jessica Parker. The two woman approached the interns with smiles on their faces._

 _"Good evening girls," Ursula greeted. "I hope all is going according to plan. I want everything to be spectacular tonight. You've impressed me thus far and I would hate for one slip up to ruin that."_

 _Charlotte and Sienna's nerves were kicking into full gear at the meaning of Ursula's words. All the work they had put in to this Expo for the last two months would be in front of all of New York's Fashion Elite._

 _"We will be out front in the front row watching everything closely. Both of you have worked hard and it shows. We will see you after the show." SJP added seeing the girls' nervous faces._

 _"Good luck Ladies" Ursula said walking away with SJP._

 _Sienna shook her head and said, "We've got this."_

 _"You said it." Charlotte said in return. "I'll go deal with the designers and you deal with anything else that needs to be done."_

 _Sienna nods and both girl go their separate ways. Ten minutes later Charlotte had a headset on her head going over the line up._

 _"Okay people I want all models dressed and accounted for!" Charlotte ordered out._

 _She watched as all the models lined up against the wall. She felt a tap on her shoulder and saw Rafael standing beside her._

 _"Are you almost ready?" He asked._

 _"Lining them up right now and then I will signal one of the stagehands to send them down the catwalk." Charlotte said._

 _"Good cause Ursula is getting restless." Rafael said with sullen attitude._

 _"I've got everything back here under control. You go back out there and I will finish up here."_

 _With Rafael gone Charlotte walked down the line checking all the models until she saw the girl that had bumped into her earlier today. The girl smiled at her briefly as the designer was stitching the dress last minute._

 _Once Charlotte had checked with the designers she walked to the front and yelled,_

 _"Okay we are going off in one minute. Designers step away from the models. We are going live in 5... 4... 3... 2... 1... Sending models down runway." Charlotte said with a smile as "Feedback" by Janet Jackson begun to play._

 _(Time Skip)_

 _Charlotte was clapping as the models did the final walk on the runway and returned backstage. She was happy that it was all over and now came the responses from the critics. The only person's opinion she was nervous to hear was Ursula's. Charlotte returned to the front_

 _Charlotte was heading for Ursula when she saw Tristan smile at her as he approached her._

 _"What did you think?" Charlotte asked nervously._

 _"It was perfect just like you," Tristan complimented as he pulled you into his arms. "I'm proud of you."_

 _Charlotte looked up into his eyes before putting her arms around his neck. She placed her lips on his and the pulled away._

 _"What was that for?" He asked._

 _"For believing in me." Charlotte said as she pulled away from him. "I'm going to go and find Ursula. I'll meet you back here in a few minutes."_

 _"Go and mingle with your success." Tristan says with a smirk._

 _Charlotte leaves Tristan and heads for the judges table. As she gets to the table she sees Ursula sitting down with Francine Hayden. It still unnerved her, that she was trying to be civil with Francine._

 _"Charlotte everything went wonderful." Ursula praised. "From what people have told me this was a success. I can't wait to see the reviews."_

 _"Thank you, Ursula. None of this wouldn't be happening if you had not given me the chance." Charlotte says._

 _"It was well organized." Francine added with a polite smile. Francine hands Charlotte a card and flowers. "Christopher sends his appreciation. He wanted to be here but I thought it was best he wasn't."_

 _"I appreciate him not coming. Thank you for giving him that advice." Charlotte replied._

 _Ursula seeing the awkward tension changes the subject, "Charlotte now that the expo was a success and we've picked the designers whose work will be shown. Starting tomorrow we will finish the Gala planning. I need mockups before the end of the week."_

 _"Sienna and I will start on it tomorrow. Is there anything else that needs to be taken care of?"_

 _"No all I can say I job well done. We will talk tomorrow."_

 _"Goodnight Ursula," Charlotte said. She then turned to Francine who was gazing at her closely. "Thank you for the flowers and for keeping Christopher away. Have a good night." Charlotte added as she walked away from the two women._

 _Once Charlotte was away from the judges table she saw Sienna, Ethan and Ethan's mother Olivia by the buffet tables. She waved towards them as she looked for Tristan. When she found her boyfriend, he was talking to a blonde girl. Charlotte briefly recognized the girl as she approached them._

 _"Tristan," Charlotte said as she stood next to her boyfriend. He glanced at her with a look, a look that she had never seen before on his face. "Is everything okay?"_

 _Before Tristan could respond the girl answered, "Hi I'm Fiona. We met briefly earlier today."_

 _"Yeah I remember." Charlotte said looking at Tristan's face then Fiona's. "Do you two know each other?"_

 _"Our families are close." Tristan spoke vaguely not looking at Charlotte._

 _"Is there something I don't know about? You're acting very weird and it's pissing me off." Charlotte said with confusion and anger in her voice. "What aren't you telling me?"_

 _"You didn't tell her." Fiona said with wide eyes at Tristan._

 _"Fiona can I speak to Charlotte alone." Tristan said in a tone that meant business._

 _Fiona picked up her flute of champagne, "It was nice to see you Tristan and good luck with everything." Fiona walked away from the table leaving the couple alone. The tension around them was weird and it was elevating the more silence there was._

 _"Tristan your scaring me." Charlotte said. "Just spit it out."_

 _Tristan wiped his face and then stared at Charlotte's eyes. "What I am about to say might change whatever is going on between us. I was trying to find the time to tell you..." He said struggling with words._

 _"Did you cheat on me? She asked._

 _"NO!" Tristan exclaimed. "This happened six months after I left. My parents wanted me to be with someone from society. Fiona and I were friends at first but we were engaged."_

 _"Stop." Charlotte said backing away from him. "Are you telling me that you were engaged a year and a half ago. You weren't going to tell me until later on when you felt like it."_

 _"Charlotte," Tristan said coming closer to her._

 _"Stay away from me." Charlotte said distraught. She swiftly turned around and walked towards Ethan and Sienna._

 _"I'm leaving and I can't deal with all of this right now" Charlotte said on the verge of tears. "He was going to get married."_

 _"Charlotte what are you talking about?" Ethan questioned as Sienna led them out of the room in the hallway._

 _"Tristan was engaged, I had to find out by meeting the ex-fiancé tonight. She was one of the models on the runway."_

 _Sienna and Ethan's eyes widened in shock. They both grabbed one of Charlotte's arms and led her further away from the Expo. Soon the trio were in front of Ethan's mom's office. He opened the door and Charlotte sat down in one of the chairs._

 _"Where is Tristan now?"_

 _"Who cares," Charlotte said with rage now seeping in her voice. "I have to get out of here. I can't be here any longer."_

 _Charlotte opened the door and walked out of the office. She turned to face her friends and smiled. "I'll call you guys when I get home." Charlotte said walking away from her friends._

 _Once Charlotte was not in their sights Ethan turned to his girlfriend with a worried look. "Do you think she'll be okay?"_

 _"I don't know Ethan. She's in shock and she needs the time to get over things." Sienna answered with worry._

 _A few minutes later, Charlotte was just about to leave the school when she saw Tristan waiting for her at the entrance. He was gazing at her with desperation, waiting for her to say something, only this time she didn't have anything to say._

 _"Char, we have to talk about this." He pleaded._

 _I don't want to talk about this." Charlotte exclaimed. "I know we don't know what happened to each other while we were apart but to find out you were engaged is something else. You couldn't tell me at all."_

 _"I'm sorry." He said weakly._

 _Charlotte wiped her face as tears cascaded down her face. "I need time and I can't do this right now."_

 _Tristan nodded and walked towards his car. He opened the car door and looked to Charlotte. "For what it's worth, I wanted to tell you on my terms. Maybe is wasn't right for me to do that but I wanted to spare you any heartache."_

 _"Mission accomplished." Charlotte bitterly replied._

 _"Good night Charlotte," Tristan said getting in his car and pulling off. He looked in his rearview and saw her walk the other way disappearing in the New York City crowd._

 _(Time Skip)_

 _Jess, Dave and Michelle were sitting in the living room waiting for Charlotte. Ethan had called Jess as soon as Charlotte left and explained everything that had happened tonight. That was four hours ago and it was close to one in the morning._

 _"Where could she be?" Michelle said with annoyance._

 _"Just relax." Jess said as he heard the doorknob turn showing Charlotte entering the apartment._

 _Charlotte closed the door and looked at her friends and saw their faces. She took off her jacket and hung it up on the hook by the door and headed straight for the kitchen. She was about to open the fridge when a hand grabbed hers._

 _"You're not going to say anything?" Michelle questioned irate. "The expo ended hours ago and we had no idea where you were."_

 _"Can we not do this right now? I have too much on my mind and I can't deal with this." Charlotte said with exhaustion._

 _"WHERE WERE YOU?!"_

 _"I was walking around and because of some of the events happening around town I was stuck on the subway. I tried calling but my phone was dead. I've had a horrible night that should have been perfect." Charlotte said as she nudged Michelle's hand away from the fridge as she pulled out the ice cream. "Right now, I just want to crawl in my bed and just pass out."_

 _Charlotte walked out of the kitchen and headed straight for her room closing the door. Michelle and Jess looked at each other with confusion and worry."_

 _(Flashback end)_

"Now you know what happened." Charlotte said to Rory and her mother.

"You could've called us and we would have wallowed with you." Lorelai said as she rubbed her daughter's arm.

Charlotte sighed as she moved her arm away from her mother, "Wallowing is you and Rory's thing. I never really did that and I don't want to now."

Lorelai and Rory exchanged baffled looks and turned back to Charlotte, "What's the plan now?" Rory asked.

"I told him I need to think and he asked me if we are breaking up." Charlotte said vaguely as the waiter returned with their food.

"And?" Michelle asked curiously as everyone looked at with hesitation.

"I have things to think over. You'll know when I have an answer. Now how about we enjoy this food and go from them." Charlotte said taking a bite of her burger.

(Time Skip)

Charlotte was going through her closet as Rory was on her bed. Charlotte was looking for an outfit for her meeting with Tristan and Rory was supposed to be helping her. Instead, Rory kept glancing at her sister and it was getting on Charlotte's nerves.

"You've been staring at me since we left the restaurant. Do you have something you'd like to ask me?" Charlotte said putting down her sweaters.

"Do you think your relationship has changed?" Rory asked softly.

"Absolutely." Charlotte said instantly. "We need to talk about the things we are afraid to talk about. That was the downfall of our relationship from before."

"If you know you have trust issues when it comes to him why are you trying to be in a relationship with him?"

"That's like me asking you why did you stick with Jess? You knew there was a problem with communication yet you stayed with him." Charlotte said with satisfaction at seeing her sister wince with agreement. "Don't throw stones if you live in glass houses."

"How can you still try with him is my question?"

"Because I love him." Charlotte admitted not looking at her sister's face.

"Charlotte?"

"I think that is the first time I have ever said it out loud. I haven't even said it to him and that's what keeps me from ending things." Charlotte explained as she heard a knock on her door. "Come in."

Lorelai opened the door and saw all the clothes on the bed. "You giving Rory clothes? I want clothes?"

"No, she's not. She wanted my opinion on what to wear when she meets with Tristan." Rory said to Lorelai as Charlotte pulled out a leather skirt.

"I have a skirt just like that." Lorelai acknowledged.

"I know you gave it to me and said ' _this would look great with your mannequin body'."_

"Well I do give great fashion advice" Lorelai smirked making them shake their heads at their mother and her antics.

"On another note, Michelle invited us to go to her dad's cabin up in Vermont. I wanted to ask if you and Lane wanted to come."

"Who else is going?" Rory asked.

"Well Michelle, Jess, Sienna, Ethan, Dave, and Myself so far." Charlotte said as she pulled out a silver top.

"Sure, can I bring Paris as well?" Rory asked.

"Your responsible for her and her actions," Charlotte quipped making Rory throw a pillow at her.

"If things go great at this sit down with Tristan will you bring him?"

"That depends on how I feel after we sit down." Charlotte replied as she saw her mother trying on clothes. "You better put them back exactly as you found them."

"But there so pretty," Lorelai exclaimed.

"They're pretty because I take care of them." She said just as Jess opens her door.

"I come bearing coffee" Jess announces as he hands one to each of them.

"If only Luke was a generous," Lorelai said making all three Gilmores sigh with delight.

"Jess shakes his head with a smirk, "You're all cracked."

"Your just now realizing this?" Rory says making Jess gaze at her intently.

He nods and walks out of the room making Lorelai whistle. "That was awkward in so many ways."

*The next chapter will be titled "Cabin Getaway." I am just about finished with re-writing part one of the crossover. That will be up probably in February seeing as I have so much crap to get through with the other two parts.

*Jess and Rory will finally air things out and try to be civil with each other. Charlotte and Tristan will discuss the future of their relationship. Lane and Dave will reunite as well as the group dealing with Paris Gellar.

*The song(s) are as follow

 _"Soulmate" by Natasha Bedingfield_

PLEASE FOLLOW FAVORITE & REVIEW

CHAZ746


	16. Cabin Getaway

**The Copyrights of this show belong to Amy Sherman-Palladino & Warner Bros. All I own is the Plot and the Original Characters.**

The Life & Times of Charlotte Gilmore Chapter 14: Cabin Getaway

It was a crisp fall morning as Charlotte and Jess were sitting on a bench in Washington Square Park. They both decided to get out of the apartment to get some fresh air. Since they had arrived at the park, Charlotte had noticed that Jess was writing in a notebook lately and was curious.

"What are you writing?" She asked curiously staring at him as he wrote.

"Just stuff." Jess replied vaguely. "It's just a bunch of my thoughts.

"Is it about a certain blue-eyed girl?" Charlotte asked receiving a glare. "Because I can help you with those thoughts."

Jess stopped writing and closed the notebook. "I don't know what to say to her." Jess admitted. "I can't find the words to say to Rory. I know I should apologize, but I feel like it's not enough."

"Well do what you do best," Charlotte said. Jess stared at her like she was from mars which made her chuckle. "With all the reading you and she have done, you mean to tell me you can't find a romantic apology?"

Jess grasped his hair in frustration and grunted. He lifted the notebook and gave it to her. "Just give it a look." Charlotte took the book and opened to the first page. For five minutes they sat in silence and Jess was nervous. Finally, Charlotte looked up at him with weird expression on her face.

"What do you think?" He asked shifting on the bench.

"Jess this is incredible." Charlotte praised.

Jess took the book from her and shook his head. "You're just saying that."

"I'm being serious. You've got a way with words and only someone like Rory would appreciate that. Just write something that you know Rory would love."

Jess looked away from Charlotte as he felt himself blush. "Whatever," He said making Charlotte playfully shove him. "Is everything ready for this weekend?"

"Michelle said she's got everything covered. She ordered a party bus to drive us all the way there. To make it easier Paris, Lane, and Rory are having a sleepover the night before we pick them up."

Jess nodded and gazed at her for a second then opened his book.

"What was that look for?"

"Huh?"

"Jess," Charlotte sternly voiced. "Why were you staring at me like that?"

"Since we are talking about relationships..." Jess hesitantly started as he closed his notebook once more. "What are you going to do about Tristan?"

Charlotte cringed on the inside at the question. She still hadn't come up with a decision and it was getting harder to figure out. It had been several days since she spoke to Tristan and Charlotte was missing him.

"I haven't decided anything."

"Look take it from a guy who has messed up several times with a girl out of his league, if you truly like the guy forgive him. You'll only regret the choice of what could have been." Jess said as Charlotte looked at him with awe.

"Those are the type of words you should be writing down to tell Rory." Charlotte said with a smirk.

"Shut up," He said as Charlotte laughed at the glare he gave her.

(Time Skip)

The next day, Charlotte looked out the window as the bus pulled up in front of her childhood home. She turned to Michelle who was on the phone. "I'm going to get Rory and the girls," Charlotte said to her friend who nodded as she continued speaking on the phone.

She walked pass Sienna who was sleeping on Ethan's right shoulder, while he was playing his Gameboy. She glanced over to the other side to see Dave fixing the strings on his guitar. He had been doing that since he got on the bus. She continued down the aisle until she saw Jess who was reading on of his many books. He looked up to her with a raised eyebrow.

"What?" He asked moodily.

"I'm going to inside the house. Do you want to come with me?" She asked him.

"No," Jess answered as he returned to reading his book.

Charlotte rolled her eyes at Jess and his ways. She knew he was really nervous about being trapped with Rory on a bus for the next four hours. "Whatever," She said to him as she stepped off the bus. As she approached the front porch, Lorelai opened the door.

"Fruit of my loins," Lorelai greeted as she hugged Charlotte who grimaced at the greeting. "You look good."

"You just saw me a few days ago," Charlotte said with a chuckle. "Where's Rory, Lane, & Paris?"

"They should be in Rory's room." Lorelai said as she led her daughter into the kitchen. "Want some coffee?"

"I have a whole Dunkin Donuts jug to myself on the bus." Charlotte answered as she knocked on Rory's door. Rory opened her door with Paris and Lane behind her. All their luggage was in front of Rory's bed.

"Hey guys," Charlotte said as she hugged Rory and Lane. "Do you need help with your stuff?"

"I can handle my own things," Paris said in her aggressive tone. Rory and Lane shook their heads at the blonde girl's abrasive attitude towards Charlotte. It was no secret to Rory that Paris was jealous of Charlotte and Tristan's relationship. Paris had a huge crush on Tristan and when she found out he was dating Charlotte, she didn't take it well.

"Nice to see you too Paris," Charlotte replied sarcastically.

Lorelai seeing the tension between Charlotte and Paris tried to defuse the situation, "So you guys ready to hit the road?" She asked.

"Yeah, thankfully Michelle had planned out everything. What are you going to do while were gone?" Charlotte said.

"Sookie and I have a couple events to plan for." Lorelai said

"Speaking of," Charlotte said going into her bag and pulling out an envelope. She hands it to her mom. "That is the check for the Gala."

"Thanks sweets, Lorelai said reading the check. Her eyebrows raised a bit before looking back to Charlotte with confusion on her face. "Char I think there is a mistake with the check. There is one to many zeros."

"Ursula was pleased with every appetizer and dish that she gave you a bonus. She also recommended you to a few of her upper echelon friends. Expect a few calls in the near future." Charlotte said with smile towards her mother.

"I have to go tell Sookie," Lorelai said as she hugged Charlotte and Rory. "Call me when you reach there. I love you girls." Lorelai added as the front door slammed.

Well let's go before Michelle realizes how long we were taking." Charlotte said leading the girls outside. Once they were outside, Dave and Ethan came off the bus.

"Dave?" Lane said in shock as she turned to Rory and Charlotte who smiled at her.

"Hey Lane," Dave said happily as he hugged her.

"What are you doing here?" Lane questioned still in shock.

"I live in New York now. I ran into Jess and we've been hanging out. Fast forward to now I am standing in front of you. It's really good to see you Lane." Dave explained as he took Lane's bag. "How's your mom?" he asked as they went on the bus.

Charlotte looked away from Lane and Dave to see Jess in the bus window staring at Rory. She saw his eyes move from Rory to hers and she smiled sadly at him. He nodded and moved away from the window.

"Charlotte?"

Charlotte turned to her sister, "Yeah?"

"What were you staring at?"

"I was thinking about Jess." Charlotte replied seeing Rory stiffen at her ex-boyfriend's name. "Are you going to be okay with being around him?"

"I don't know," Rory spoke softly.

"Eventually you are going to have speak with him. Right?" Charlotte said. Charlotte then watched as Rory's face turn angrily.

"I don't think you should be telling me who to talk to. You can't even decide if you want to try and be with Tristan. Until you can make up your mind on your relationship don't but into whatever is going on with me and Jess." Rory stated as she grabbed her bag and went on the bus. Paris glared at Charlotte as she followed Rory on the bus.

Charlotte turned to Ethan, "This going to be a long bus ride."

"Four hours of unwanted tension. This is going to be the best." He said sarcastically as he walked on the bus with Charlotte sighing behind him.

(Time Skip)

A couple hours had passed since they had left Stars Hollow, and Rory had ignored Charlotte the entire bus ride. Charlotte listened to Rory and Paris talk about the Yale Newspaper.

"How long do you plan on staring at your sister?" Michelle asked her best friend.

"Something Rory said has been bugging me." Charlotte said as she turned to friend. "Do you think I am a hypocrite for telling Rory she needs to talk Jess? She said until I know what I want from Tristan I should mind my business."

"I think you should stay out of whatever is going on between Rory and Jess." Michelle said. "Rory is right about what she said. Until you make a decision going forward about Tristan, you have no room to judge."

"I just want my friend to be happy."

"What about Rory's happiness?" Michelle questioned seeing the look of understanding flash on Charlotte's face.

"I didn't think about Rory. I was so focused on Jess and how he was feeling. I'm around him more than I am with Rory."

Michelle put her phone down and gave her friend her full attention. "You're a good friend Char, but you and Rory have been growing distant since we moved to New York. Take this weekend to try and reconnect with your sister."

Charlotte thought about Michelle's words and realized to some degree, she and Rory had drifted and weren't as close as they once were. She knew on some level that was her doing. Being constantly compared to your sister who excelled at everything academically kind of put a damper on being close. It wasn't that she hated her sister, it was more of the fact that she was trying to find out who she was without the _"Why can't you be like your sister?"_ label.

"I'll try." Charlotte said.

"I hope so." Michelle said going back to her phone.

"On another note, where is Quinn?" Charlotte asked trying to change the subject.

"Quinn is working all weekend. But he promised to make it up by taking me to dinner." Michelle says picking up her phone, "Just because you changed the subject doesn't mean you are off the hook. Apologize to Rory and stay out of her business unless she asks for your opinion."

"I hate when you're right," Charlotte quips with a smile.

"Whatever," Michelle says dialing Quinn once more.

(Time Skip)

After hours of sitting on a bus they had finally reached the cabin. Once the bus stopped we all slowly got off the bus. Michelle stood in front of the cabin facing us with a smile. Charlotte was exhausted and all she wanted to do was take a hot shower and get some sleep.

"Okay guys there are five rooms. I am taking the master bedroom, Charlotte is taking the room beside mine, Paris, Rory, Lane take one of the rooms upstairs. Jess and Dave, you will take the room across from theirs. Finally, Ethan and Sienna will take the last room." Michelle instructed as we all began to take our bags and head inside the house.

"This place is nice!" Sienna praised as they all looked around the cabin living room.

"Luckily daddy's third wife knows how to pick vacation homes." Michelle bitterly stated as she walked down the left hallway with her bags. "You all know where your staying. So, hurry up and get yourselves settled." She added as her voice faded down the hallway.

Charlotte picked up her bag and walked to her room. When she reached the room her cell phone rang. She saw the called id and took a deep breath.

"Hi," She answered softly as she sat on the bed.

"I wasn't sure you were going to call me so I made the first move." Tristan said. "Are you free to talk?"

Charlotte looked at the hallway and saw no one there. "I'm free," Charlotte said as she tucked a strand of hair behind her ear. "I'm sorry for not calling you. I just haven't made a decision yet and I don't want to make a wrong choice."

"I get it," Tristan says. "It isn't an easy choice to make. Whatever you decide I still want to be in your life."

"What are you saying?"

"I'm saying I'll go with whatever you decide. I've hurt you more times that I can count." Tristan explains.

"You've only hurt me two times."

"You keep count?' He asked. Charlotte smiled as she imagined him with his smirk on his face.

"You do know that you're my first and only boyfriend. Every girl remembers their first in every way." Charlotte replies as she looks out the window to see it start snowing. She hears him chuckle and continues. "What are you doing right now?"

"I'm just getting out of class and heading home. I was going to heat up some left overs and study. Why you want to do something together?" Tristan asks hopefully.

"Even if I wanted to the answer is no. I'm in Vermont for the weekend with everybody. But we could do something Wednesday night after work."

"I like the sound of that. Listen I have to go, can I call you later?" He asked.

Charlotte looked down at the phone for a few seconds before saying, "Okay,"

"Alright. Bye Charlotte." Tristan said before hanging up.

Charlotte stared at the phone once more before placing it on the bed. She laid down on the bed exhausted from the ride and from talking with Tristan. Hearing Tristan's voice had lessened the pain he caused and it made her miss him more. She was still confused and was no closer to making a decision.

"Charlotte?"

Charlotte turned her head to the doorway to see Jess looking at her. "You okay?" He asked as he sat on the bed.

"I will be." She said as she realized he was still there. "Was there something you needed?" She asked.

"Ethan and Michelle are making chili. I wanted to see if you were hungry." Jess explained.

"When have I not been able to eat?" Charlotte questioned coyly.

"My mistake I forget Gilmore's have bottomless pits inside them." Jess added as he walked out of the room.

"And don't you forget it," Charlotte called after him as she stood up from the bed and followed after him.

(Time Skip)

It was late at night as Jess sat on one of the sofas with his notebook in his lap. He needed to get out of the room as Dave was snoring in his sleep. After talking with Charlotte, Jess was nervous and anxious about speaking with Rory. He had no idea what to say to her and it was pissing him off.

Jess was so deep in thoughts he didn't see Rory come into the living room. She stopped at the hallway entrance and saw him sitting quietly staring at the page he was gripping tightly.

"Jess?" She called out softly.

Jess looked up from his book to see Rory standing beside him. She was worried from the look on her face. He ran his hand through his hair as he stood up. "Hey, what are you doing up?"

"I couldn't sleep and I was thinking of talking to Charlotte."

"Are you still mad at her?"

"I'm not mad at her," Rory denied. She sat on the couch and saw Jess's notebook open. "What are you writing about?" asked changing the subject.

Jess smirked at her lame excuse to change the subject. He moved closer to her as he picked up the book. "Just writing somethings." He answered vaguely.

"Like what?' Rory asked as she turned to face him.

Jess shifted in his seat and stared into Rory's eyes. That innocence she held was there but it was slightly dimmer. It always made Jess safe and insecure in that same moment. "It is about me and the things I've gone through in my life." Jess explained.

"You're writing a book about yourself? Jess that is _great_!" Rory said gushing with excitement.

Jess shifted in nervousness, "Relax, it's still in the planning stages. I'm just jotting my thoughts down so I can make it in to something eventually." He explained but Rory was still dazzling him with that look of undeserved praise.

"Jess I knew if you put your mind to something..." Rory started to say before she stopped and stood up.

"Rory?" Jess questioned.

"Why did you leave?" She asked making him turn away from her.

"I don't know," He answered not facing her. "I just had to leave."

"You couldn't even tell me you were leaving. That made me feel like I didn't mean anything to you."

Jess swiftly stood up and turned to her. He saw the tears slowly streaming down her face. "Rory," He said softly as he walked closer to her.

Rory looked him directly in the face, "Why do you always run when things get hard? Why can't you face it head on?"

"Because I'm afraid if I let anyone close, they'll hurt me!" Jess screamed making Rory take a few steps away from him. "You don't know what I've been through. I am trying to fix my life anyway I can. I am sorry for hurting you and I mean that sincerely. I love you Rory and I am willing to just be friends. I am tired of hurting the people I love." Jess says breathing heavy.

Rory stares at him and says, "I love you too."

"Where do we go from here?" He asks.

"I think we need to be friends and go from there." Rory states seeing the morose look on Jess's face. "We have a lot of problems we need to get through. I want to be with you but I'm not willing to be broken again."

"So, we're friends?" he asked.

"For now, and maybe more in the future. Until we fix our communication problem." Rory explained once more.

Jess nodded and handed her his notebook. "This will help clear the air. It's just a few moments from when I was growing up. Charlotte already read some of it but I wanted your opinion as well." Jess said as Rory carefully took the book from him with a smile.

(Time Skip)

The next morning, Charlotte walked out of her room and slowly headed for the kitchen. She saw Jess and Rory on the couch sleeping next to each other. She smiled at the sight but was a little hurt for some reason. Charlotte walked into the kitchen and began to make breakfast for herself.

A few minutes later Rory entered the kitchen and just stared at Charlotte. "Morning," Rory greeted as she grabbed herself a cup of coffee.

"Morning," Charlotte said in return as she ate her bagel. She picked up her bagel plate and was about to walk out of the kitchen until Rory called her name. Charlotte turned around and faced her sister.

"I'm sorry," Rory says in whisper.

"What do you have to be sorry for? I am the one who was pushing you to talk to Jess." Charlotte said.

Rory patted the stool next to her and once Charlotte sat down, she continued, "You are not the only one who has told me to talk with Jess. Paris and Mom surprisingly said I needed to talk with Jess and go from there."

"I wasn't thinking about you when I was asking for you to talk with Jess." Charlotte explained. She saw the perplexed expression on Rory's face and decided to explain further. "I never thought about your feelings in this entire situation. I only thought about Jess because we've spoken a lot about you and him. I kept telling him if he wants to finally be happy, he has to admit his wrongs and own up to his problems."

Rory sipped her coffee and nodded her head.

"Say something," Charlotte said. "Tell me what you are thinking?"

"I think you're a good friend and Jess is lucky to have you as a friend." Rory finally says. "We spoke last night." Rory adds with small smile.

"I noticed because I saw you two sleeping on the couch with one another. Give me the details because I am dying over here. Are you two back together?" Charlotte asks.

Rory shakes her head, "No we have a lot of things to work on but we are friends and maybe something more later on down the line."

"Are you okay?"

"I get why he acts the way he does but I just wish he would stop running." Rory states with frustration.

"At least you know where he is sleeping," Charlotte points out as she gives the other half of her bagel to Rory. Rory laughs as she takes the bagel and they sit quietly and eat. While they were eating Jess walked into the kitchen scratching his head.

"Hey sleepyhead," Rory and Charlotte greeted receiving a grunt from Jess.

They watched him pour himself a cup of coffee and then sit across from them. After he had taken a few gulps, Jess was more awake. "What are you guys doing up so early?" He asked in a tired voice.

"Just talking," Rory said vaguely. She glances at Charlotte who gets the message and stands up from her stool.

"Well I am going to go and finish my work. I'll see you guys for lunch." Charlotte said hugging Rory and walked out of the kitchen.

(Time Skip)

Charlotte was in her room going over the plans for the Gala. She had been looking at models of the room and how to organize the designers works throughout the room. She was trying to showcase everything evenly so everyone got a chance to preview everything.

A knock on her door broke her concentration. "Come in," She called out while staring at a diagram.

"Hey you still working?" Sienna and Michelle asked as they came in the room.

Charlotte looked away from her work to see her friends with food in their hands. "Yeah I finished my homework a couple of hours ago. I've been working on the layout for the Gala and how Ursula wants it setup."

"I'll give you my notes later for my input." Sienna offers as she looks over what Charlotte had done. "It looks like you have a general idea how you want it to go. I'm impressed and hopefully Rafael and Ursula will be too."

"Enough about work," Michelle cut them off. "I heard you speak with Tristan yesterday. I wanted to give you some space before I asked what is going on."

Charlotte smiled at her best friend, "We're having dinner when we get back to the city."

"Have you made a decision yet?" Sienna asked as Michelle looks at her wondering the same.

"Not yet," She replies.

"What's holding you back?"

"I'm struggling with the trust issue and whether or not I will believe him." Charlotte says as her friends nod with understanding.

Michelle hands her a plate with a sandwich, "You can't make these kinds of decisions on an empty stomach."

"When are you supposed to meet him?" Sienna asks.

"He is picking me up from work on Wednesday. That gives me two days to come to a decision." Charlotte says as she glances at the Gala diagram once more.

"I'm so glad things with Ethan are still new." Sienna says happily as Charlotte and Michelle smile at her.

"I know exactly what you mean. That new feeling when you start dating someone. Everything feels right and you're on the same wave length."

"Enjoy it while it lasts." Charlotte quips as Sienna throws a celery stick at her.

 ***The next chapter will be titled "Family Intervention" and I am still working on the Gala Crossover.**

 ***Charlotte meets with her mother for dinner only to see Christopher sitting at the table as well.**

 ***Rory visits New York with Lane to hang out with Jess and Dave. Only old resentments come to the forefront and ruin a good time.**

 **On another note, I know I haven't updated this story in close to a year but I really appreciate all the support I've gotten for all my stories. I have a lot of things going on in my life and this takes me out of my reality for a brief moment to decompress. I just want to take the time out an thank each and every one of you.**

 **PLEASE FOLLOW, FAVORITE & REVIEW**

 **Chaz746**


	17. Author Message 2

**Author's Message 2:**

 **Lately I've been rereading "Digimon 02 Redux" & "When All Is Said & Done. I feel like I have lost interest in the first one and a friend of mine gave me an idea for the second one. Tune in for the updates **

**Please Follow, Favorite, & Review my other fanfics**

" **The Life & Times of Charlotte Gilmore"**

" **Reasons"**

" **Logan Grey: The Long Lost Brother"**

" **Scion: Agent of S.H.I.E.L.D."**

" **NCIS: Seattle"**

" **Fallen Kingdom"**

 **Chaz746**


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